A NEW METHOD FOR THE PREPARATION OF DIARYLPHTHALIDES1

FF Blicke, OJ Weinkauff

Index: Blicke; Weinkauff Journal of the American Chemical Society, 1932 , vol. 54, p. 1446,1451

Full Text: HTML

Citation Number: 10

Abstract

We have not been able by the use of the method described above to prepare certain mono- and dihydroxydiarylphthalides although the syntheses of the corresponding tertiary carbinols have been described in the experimental part of the paper; in some cases the compounds seemed to decompose during the oxidation of the side chain, in others during demethylation. The applicability of the procedure for the preparation of a number of other ...

 Related Synthetic Route
2-(4-Hydroxybenzoyl)benzoic acid Structure

85-57-4

2-(4-Hydroxyben...

~%

2-[(4-methoxyphenyl)methyl]benzoic acid Structure

5398-17-4

2-[(4-methoxyph...

Phenol Structure

108-95-2

Phenol

~%

2-[(4-methoxyphenyl)methyl]benzoic acid Structure

5398-17-4

2-[(4-methoxyph...

2-[(4-hydroxyphenyl)methyl]benzoic acid Structure

14660-14-1

2-[(4-hydroxyph...

Dimethyl sulfate Structure

77-78-1

Dimethyl sulfate

~%

2-[(4-methoxyphenyl)methyl]benzoic acid Structure

5398-17-4

2-[(4-methoxyph...

Phthalic anhydride Structure

85-44-9

Phthalic anhydride

~%

Isophenolphthalein Structure

2037-19-6

Isophenolphthalein

Phenol Structure

108-95-2

Phenol

~%

Isophenolphthalein Structure

2037-19-6

Isophenolphthalein

Anthraquinone Structure

84-65-1

Anthraquinone

magnesium,methoxybenzene,iodide Structure

112219-63-3

magnesium,metho...

~%

9(10H)-Anthracenone,10-hydroxy-10-(4-methoxyphenyl)- Structure

57028-32-7

9(10H)-Anthrace...

Phenol Structure

108-95-2

Phenol

~%

2-[(4-hydroxyphenyl)methyl]benzoic acid Structure

14660-14-1

2-[(4-hydroxyph...

Phthalic anhydride Structure

85-44-9

Phthalic anhydride

~%

2-[(4-hydroxyphenyl)methyl]benzoic acid Structure

14660-14-1

2-[(4-hydroxyph...

Xanthone Structure

90-47-1

Xanthone

~%

9H-Xanthen-9-ol,9-[2-(ethoxymethyl)phenyl]- Structure

6315-83-9

9H-Xanthen-9-ol...

Xanthone Structure

90-47-1

Xanthone

~%

spiro(isobenzofuran-1(3H),9'-xanthen)-3-one Structure

596-24-7

spiro(isobenzof...

9H-Xanthen-9-ol,9-(2-methylphenyl)- Structure

6315-73-7

9H-Xanthen-9-ol...

~%

spiro(isobenzofuran-1(3H),9'-xanthen)-3-one Structure

596-24-7

spiro(isobenzof...

9H-Xanthen-9-ol,9-[2-(ethoxymethyl)phenyl]- Structure

6315-83-9

9H-Xanthen-9-ol...

~%

spiro(isobenzofuran-1(3H),9'-xanthen)-3-one Structure

596-24-7

spiro(isobenzof...

o-tolylmagnesium bromide Structure

932-31-0

o-tolylmagnesiu...

~%

spiro(isobenzofuran-1(3H),9'-xanthen)-3-one Structure

596-24-7

spiro(isobenzof...

2,2'-DIMETHOXYBENZOPHENONE Structure

13102-33-5

2,2'-DIMETHOXYB...

~%

spiro(isobenzofuran-1(3H),9'-xanthen)-3-one Structure

596-24-7

spiro(isobenzof...

Benzenemethanol,2-(ethoxymethyl)-a,a-bis(2-methoxyphenyl)- Structure

5460-75-3

Benzenemethanol...

~%

spiro(isobenzofuran-1(3H),9'-xanthen)-3-one Structure

596-24-7

spiro(isobenzof...

9H-Xanthen-9-ol,9-[2-(ethoxymethyl)phenyl]- Structure

6315-83-9

9H-Xanthen-9-ol...

acetic acid Structure

64-19-7

acetic acid

~%

spiro(isobenzofuran-1(3H),9'-xanthen)-3-one Structure

596-24-7

spiro(isobenzof...

Benzophenone Structure

119-61-9

Benzophenone

~%

[2-(ethoxymethyl)phenyl]-diphenyl-methanol Structure

5437-91-2

[2-(ethoxymethy...

[2-(ethoxymethyl)phenyl]-diphenyl-methanol Structure

5437-91-2

[2-(ethoxymethy...

~%

Kastle-Meyer reagent Structure

596-29-2

Kastle-Meyer reagent

Benzophenone Structure

119-61-9

Benzophenone

~%

Kastle-Meyer reagent Structure

596-29-2

Kastle-Meyer reagent

(2-methylphenyl)-diphenyl-methanol Structure

5432-54-2

(2-methylphenyl...

Sulfuric acid Structure

7664-93-9

Sulfuric acid

~%

Kastle-Meyer reagent Structure

596-29-2

Kastle-Meyer reagent

[2-(ethoxymethyl)phenyl]-diphenyl-methanol Structure

5437-91-2

[2-(ethoxymethy...

acetic acid Structure

64-19-7

acetic acid

~%

Kastle-Meyer reagent Structure

596-29-2

Kastle-Meyer reagent

2,4'-Dimethoxybenzophenone Structure

5449-69-4

2,4'-Dimethoxyb...

~%

Benzenemethanol,2-(ethoxymethyl)-a-(2-methoxyphenyl)-a-(4-methoxyphenyl)- Structure

6636-18-6

Benzenemethanol...

N/A Structure

500286-49-7

N/A

~%

9-Anthracenol,9,10-dihydro-3-methoxy-9,10,10-tris(4-methoxyphenyl)- Structure

7477-41-0

9-Anthracenol,9...

2-(4-Hydroxybenzoyl)benzoic acid Structure

85-57-4

2-(4-Hydroxyben...

~%

9-Anthracenol,9,10-dihydro-3-methoxy-9,10,10-tris(4-methoxyphenyl)- Structure

7477-41-0

9-Anthracenol,9...

2-[(4-methoxyphenyl)methyl]benzoic acid Structure

5398-17-4

2-[(4-methoxyph...

~%

9-Anthracenol,9,10-dihydro-3-methoxy-9,10,10-tris(4-methoxyphenyl)- Structure

7477-41-0

9-Anthracenol,9...

2-[(4-hydroxyphenyl)methyl]benzoic acid Structure

14660-14-1

2-[(4-hydroxyph...

~%

9-Anthracenol,9,10-dihydro-3-methoxy-9,10,10-tris(4-methoxyphenyl)- Structure

7477-41-0

9-Anthracenol,9...

2-(4-methoxy-benzyl)-benzoic acid ethyl ester Structure

500282-70-2

2-(4-methoxy-be...

~%

9-Anthracenol,9,10-dihydro-3-methoxy-9,10,10-tris(4-methoxyphenyl)- Structure

7477-41-0

9-Anthracenol,9...

N/A Structure

500346-79-2

N/A

~%

9-Anthracenol,9,10-dihydro-3-methoxy-9,10,10-tris(4-methoxyphenyl)- Structure

7477-41-0

9-Anthracenol,9...

1-(4-Methoxy-benzyl)-2-(α-hydroxy-4.4'-dimethoxy-benzhydryl)-benzol Structure

861096-86-8

1-(4-Methoxy-be...

~%

9-Anthracenol,9,10-dihydro-3-methoxy-9,10,10-tris(4-methoxyphenyl)- Structure

7477-41-0

9-Anthracenol,9...

Phenol Structure

108-95-2

Phenol

~%

9-Anthracenol,9,10-dihydro-3-methoxy-9,10,10-tris(4-methoxyphenyl)- Structure

7477-41-0

9-Anthracenol,9...

o-tolylmagnesium bromide Structure

932-31-0

o-tolylmagnesiu...

Xanthone Structure

90-47-1

Xanthone

~%

9H-Xanthen-9-ol,9-(2-methylphenyl)- Structure

6315-73-7

9H-Xanthen-9-ol...

magnesium,methoxybenzene,iodide Structure

112219-63-3

magnesium,metho...

~%

Phthalazine, 1,4-bis(4-methoxyphenyl)- Structure

5441-28-1

Phthalazine, 1,...

Phthalic anhydride Structure

85-44-9

Phthalic anhydride

~%

Phthalazine, 1,4-bis(4-methoxyphenyl)- Structure

5441-28-1

Phthalazine, 1,...

methyl 2-(4-methoxybenzoyl)benzoate Structure

5449-71-8

methyl 2-(4-met...

~%

Phthalazine, 1,4-bis(4-methoxyphenyl)- Structure

5441-28-1

Phthalazine, 1,...

Isobenzofuran,1,3-bis(4-methoxyphenyl)- Structure

6306-97-4

Isobenzofuran,1...

~%

Phthalazine, 1,4-bis(4-methoxyphenyl)- Structure

5441-28-1

Phthalazine, 1,...

2-[bis(4-methoxyphenyl)methyl]benzoic acid Structure

7477-32-9

2-[bis(4-methox...

~%

Phthalazine, 1,4-bis(4-methoxyphenyl)- Structure

5441-28-1

Phthalazine, 1,...

2-[bis(4-methoxyphenyl)methyl]benzoic acid Structure

7477-32-9

2-[bis(4-methox...

~%

Isobenzofuran,1,3-bis(4-methoxyphenyl)- Structure

6306-97-4

Isobenzofuran,1...

Sulfuric acid Structure

7664-93-9

Sulfuric acid

2-[bis(4-methoxyphenyl)methyl]benzoic acid Structure

7477-32-9

2-[bis(4-methox...

~%

Isobenzofuran,1,3-bis(4-methoxyphenyl)- Structure

6306-97-4

Isobenzofuran,1...

magnesium,methoxybenzene,iodide Structure

112219-63-3

magnesium,metho...

~%

Benzene,o-di-p-anisoyl-, dioxime (8CI) Structure

7477-30-7

Benzene,o-di-p-...

Phthalic anhydride Structure

85-44-9

Phthalic anhydride

~%

Benzene,o-di-p-anisoyl-, dioxime (8CI) Structure

7477-30-7

Benzene,o-di-p-...

methyl 2-(4-methoxybenzoyl)benzoate Structure

5449-71-8

methyl 2-(4-met...

~%

Benzene,o-di-p-anisoyl-, dioxime (8CI) Structure

7477-30-7

Benzene,o-di-p-...

Isobenzofuran,1,3-bis(4-methoxyphenyl)- Structure

6306-97-4

Isobenzofuran,1...

~%

Benzene,o-di-p-anisoyl-, dioxime (8CI) Structure

7477-30-7

Benzene,o-di-p-...

2-[bis(4-methoxyphenyl)methyl]benzoic acid Structure

7477-32-9

2-[bis(4-methox...

~%

Benzene,o-di-p-anisoyl-, dioxime (8CI) Structure

7477-30-7

Benzene,o-di-p-...

9(10H)-Anthracenone, 2-methoxy- Structure

53604-95-8

9(10H)-Anthrace...

~%

10-hydroxy-3-methoxy-10-(4-methoxyphenyl)anthracen-9-one Structure

6315-79-3

10-hydroxy-3-me...

2-METHOXYANTHRAQUINONE Structure

3274-20-2

2-METHOXYANTHRA...

magnesium,methoxybenzene,iodide Structure

112219-63-3

magnesium,metho...

~%

10-hydroxy-3-methoxy-10-(4-methoxyphenyl)anthracen-9-one Structure

6315-79-3

10-hydroxy-3-me...

Diethyl ether Structure

60-29-7

Diethyl ether

2-METHOXYANTHRAQUINONE Structure

3274-20-2

2-METHOXYANTHRA...

magnesium,methoxybenzene,iodide Structure

112219-63-3

magnesium,metho...

benzene Structure

71-43-2

benzene

~%

Detail
DMBP Structure

90-96-0

DMBP

~%

[2-(ethoxymethyl)phenyl]-bis(4-methoxyphenyl)methanol Structure

6315-85-1

[2-(ethoxymethy...

9(10H)-Anthracenone, 2-methoxy- Structure

53604-95-8

9(10H)-Anthrace...

~%

2-METHOXYANTHRAQUINONE Structure

3274-20-2

2-METHOXYANTHRA...

(3-benzoyl-4-hydroxyphenyl)(2-hydroxyphenyl)methanone Structure

102555-48-6

(3-benzoyl-4-hy...

~%

2,4'-Dihydroxybenzophenone Structure

606-12-2

2,4'-Dihydroxyb...

o-anisoyl chloride Structure

21615-34-9

o-anisoyl chloride

~%

2,4'-Dihydroxybenzophenone Structure

606-12-2

2,4'-Dihydroxyb...

Tin(IV) chloride Structure

7646-78-8

Tin(IV) chloride

Phenyl salicylate Structure

118-55-8

Phenyl salicylate

~%

2,4'-Dihydroxybenzophenone Structure

606-12-2

2,4'-Dihydroxyb...

Aluminium chloride Structure

7446-70-0

Aluminium chloride

o-anisoyl chloride Structure

21615-34-9

o-anisoyl chloride

benzene Structure

71-43-2

benzene

~%

2-Hydroxybenzophenone Structure

117-99-7

2-Hydroxybenzop...

Detail
Benzenemethanol,2-(ethoxymethyl)-a,a-bis(2-methoxyphenyl)- Structure

5460-75-3

Benzenemethanol...

~%

3,3-Bis(2-methoxyphenyl)-2-benzofuran-1(3H)-one Structure

7477-27-2

3,3-Bis(2-metho...

2,2'-DIMETHOXYBENZOPHENONE Structure

13102-33-5

2,2'-DIMETHOXYB...

~%

3,3-Bis(2-methoxyphenyl)-2-benzofuran-1(3H)-one Structure

7477-27-2

3,3-Bis(2-metho...

Benzenemethanol,2-(ethoxymethyl)-a,a-bis(2-methoxyphenyl)- Structure

5460-75-3

Benzenemethanol...

acetic acid Structure

64-19-7

acetic acid

~%

3,3-Bis(2-methoxyphenyl)-2-benzofuran-1(3H)-one Structure

7477-27-2

3,3-Bis(2-metho...

2,2'-DIMETHOXYBENZOPHENONE Structure

13102-33-5

2,2'-DIMETHOXYB...

~%

Benzenemethanol,2-(ethoxymethyl)-a,a-bis(2-methoxyphenyl)- Structure

5460-75-3

Benzenemethanol...

phenolphthalin Structure

81-90-3

phenolphthalin

Dimethyl sulfate Structure

77-78-1

Dimethyl sulfate

~%

3, 3-Bis(4-methoxyphenyl)phthalide Structure

6315-80-6

3, 3-Bis(4-meth...

o-tolylmagnesium bromide Structure

932-31-0

o-tolylmagnesiu...

2,4'-Dimethoxybenzophenone Structure

5449-69-4

2,4'-Dimethoxyb...

~%

(2-methoxyphenyl)-(4-methoxyphenyl)-(2-methylphenyl)methanol Structure

6315-84-0

(2-methoxypheny...


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