Base catalysed rearrangements of 4-hydroxyphenyl allyl ethers: syntheses of alliodorin and alliodorol

LM Harwood, AJ Oxford, C Thomson

Index: Harwood; Oxford; Thomson Journal of the Chemical Society - Series Chemical Communications, 1991 , # 18 p. 1303 - 1305

Full Text: HTML

Citation Number: 1

Abstract

The 4-hydroxyphenyl allyl ethers in refluxing aqueous methanol in the presence of KOH and oxygen furnish 2-substituted 1, 4-dihydroxybenzene derivatives; products and are derived base catalysed Claisen rearrangement, whereas presence of 3′-substitution on the allylic moiety disfavours this pathway, leading to fo

 Related Synthetic Route
4-(allyloxy)phenol Structure

6411-34-3

4-(allyloxy)phenol

~72%

2-prop-2-enylbenzene-1,4-diol Structure

5721-21-1

2-prop-2-enylbe...

(E)-4-((3,7-dimethylocta-2,6-dien-1-yl)oxy)phenol Structure

58981-41-2

(E)-4-((3,7-dim...

~%

2-prop-2-enylbenzene-1,4-diol Structure

5721-21-1

2-prop-2-enylbe...

N/A Structure

137362-24-4

N/A

~%

2-prop-2-enylbenzene-1,4-diol Structure

5721-21-1

2-prop-2-enylbe...

Hydroquinone Structure

123-31-9

Hydroquinone

~%

2-prop-2-enylbenzene-1,4-diol Structure

5721-21-1

2-prop-2-enylbe...

(E)-4-(but-2-en-1-yloxy)phenol Structure

112142-91-3

(E)-4-(but-2-en...

~63%

(2-Butenyl)-hydrochinon Structure

60449-42-5

(2-Butenyl)-hyd...

2-but-3-en-2-ylbenzene-1,4-diol Structure

101459-67-0

2-but-3-en-2-yl...

(E)-4-((3,7-dimethylocta-2,6-dien-1-yl)oxy)phenol Structure

58981-41-2

(E)-4-((3,7-dim...

~%

2-but-3-en-2-ylbenzene-1,4-diol Structure

101459-67-0

2-but-3-en-2-yl...

N/A Structure

137362-24-4

N/A

~%

2-but-3-en-2-ylbenzene-1,4-diol Structure

101459-67-0

2-but-3-en-2-yl...

Hydroquinone Structure

123-31-9

Hydroquinone

~%

2-but-3-en-2-ylbenzene-1,4-diol Structure

101459-67-0

2-but-3-en-2-yl...

N/A Structure

32328-83-9

N/A

~38%

1,4-Benzenediol, 2-(3-methyl-2-butenyl)- Structure

5919-91-5

1,4-Benzenediol...

N/A Structure

137362-25-5

N/A

Hydroquinone Structure

123-31-9

Hydroquinone

(E)-4-((3,7-dimethylocta-2,6-dien-1-yl)oxy)phenol Structure

58981-41-2

(E)-4-((3,7-dim...

~53%

geranylhydroquinone Structure

10457-66-6

geranylhydroquinone

Hydroquinone Structure

123-31-9

Hydroquinone


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