e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Oxidation of benzylic alcohols and ethers to carbonyl derivatives by nitric acid in dichloromethane

P Strazzolini, A Runcio

Index: Strazzolini, Paolo; Runcio, Antonio European Journal of Organic Chemistry, 2003 , # 3 p. 526 - 536

Full Text: HTML

Citation Number: 29

Abstract

Abstract Nitric acid in dichloromethane may be successfully employed for the oxidation of benzylic alcohols and ethers to the corresponding carbonyl compounds. The proposed method proved to be of general applicability, affording very good yields of aldehydes and ketones and showing interesting chemoselectivity in many instances, allowing competitive aromatic nitration to be avoided, as well as− in the case of aldehydes− any further ...

Benzyl acetate Structure

~%

Benzenemethanol,4-nitro-, 1-acetate Structure

Benzenemethanol...

3-Nitrobenzyl acetate Structure

3-Nitrobenzyl a...

2-nitrobenzyl acetate Structure

2-nitrobenzyl a...

1-Chloro-4-(methoxymethyl)benzene Structure

1-Chloro-4-(met...

~86%

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

Benzyln-butylether Structure

Benzyln-butylether

~0%

t-butyl nitrite Structure

t-butyl nitrite

tert-butyl nitrate Structure

tert-butyl nitrate

Benzaldehyde Structure

t-butyl nitrite Structure

t-butyl nitrite

~33%

tert-butyl nitrate Structure

tert-butyl nitrate

4-(Methoxymethyl)-benzenemethanol Structure

4-(Methoxymethy...

~81%

4-(Methoxymethyl)-benzaldehyde Structure

4-(Methoxymethy...

Terephthalaldehyde Structure

Terephthalaldehyde

Methyl 4-(methoxymethyl)benzoate Structure

Methyl 4-(metho...

~%

4-(Methoxymethyl)-benzaldehyde Structure

4-(Methoxymethy...

4-(Methoxymethyl)benzoic acid Structure

4-(Methoxymethy...

~%

4-(Methoxymethyl)-benzaldehyde Structure

4-(Methoxymethy...

1,1-dimethylethyl 4-(methoxymethyl)benzoate Structure

1,1-dimethyleth...

~%

4-(Methoxymethyl)-benzaldehyde Structure

4-(Methoxymethy...

[(2-phenylethoxy)methyl]benzene Structure

[(2-phenylethox...

~9%

2-phenylethyl nitrite Structure

2-phenylethyl n...

Phenylacetaldehyde Structure

Phenylacetaldehyde

Benzaldehyde Structure

4-(methoxymethyl)benzyl chloride Structure

4-(methoxymethy...

~93%

4-(Chloromethyl)benzaldehyde Structure

4-(Chloromethyl...

Neopentyl alcohol Structure

Neopentyl alcohol

~9%

2,2-dimethylpropyl nitrite Structure

2,2-dimethylpro...

Nitric acid 2,2-dimethylpropyl ester Structure

Nitric acid 2,2...

Pivaldehyde Structure

Detail

4-(methoxymethyl)benzyl acetate Structure

4-(methoxymethy...

~77%

Acetic acid 4-formylbenzyl ester Structure

Acetic acid 4-f...

4-(Methoxymethyl)-benzenemethanol Structure

4-(Methoxymethy...

~%

Acetic acid 4-formylbenzyl ester Structure

Acetic acid 4-f...

Methyl 4-(methoxymethyl)benzoate Structure

Methyl 4-(metho...

~%

Acetic acid 4-formylbenzyl ester Structure

Acetic acid 4-f...

4-(Methoxymethyl)benzoic acid Structure

4-(Methoxymethy...

~%

Acetic acid 4-formylbenzyl ester Structure

Acetic acid 4-f...

1,1-dimethylethyl 4-(methoxymethyl)benzoate Structure

1,1-dimethyleth...

~%

Acetic acid 4-formylbenzyl ester Structure

Acetic acid 4-f...

Benzene, 2,4-dichloro-1-(methoxymethyl) Structure

Benzene, 2,4-di...

~81%

2,4-Dichlorobenzaldehyde Structure

2,4-Dichloroben...

Neopentyl alcohol Structure

Neopentyl alcohol

~10%

2,2-dimethylpropyl nitrite Structure

2,2-dimethylpro...

Nitric acid 2,2-dimethylpropyl ester Structure

Nitric acid 2,2...

Pivaldehyde Structure

Detail

[(2-phenylethoxy)methyl]benzene Structure

[(2-phenylethox...

~33%

2-phenylethyl nitrite Structure

2-phenylethyl n...

Phenylacetaldehyde Structure

Phenylacetaldehyde

Benzaldehyde Structure

1-(Methoxymethyl)-4-(2-methyl-2-propanyl)benzene Structure

1-(Methoxymethy...

~84%

p-t-Butylbenzaldehyde Structure

p-t-Butylbenzal...

1,1-dimethylethyl 4-(methoxymethyl)benzoate Structure

1,1-dimethyleth...

~90%

4-(Methoxymethyl)benzoic acid Structure

4-(Methoxymethy...

4-(Methoxymethyl)benzoic acid Structure

4-(Methoxymethy...

~85%

4-Formylbenzoic acid Structure

4-Formylbenzoic acid

Benzyln-butylether Structure

Benzyln-butylether

~0%

t-butyl nitrite Structure

t-butyl nitrite

tert-butyl nitrate Structure

tert-butyl nitrate

Benzaldehyde Structure

1-chloro-2-(methoxymethyl)benzene Structure

1-chloro-2-(met...

~82%

2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

p-tolylmethanol Structure

p-tolylmethanol

Dimethyl sulfate Structure

Dimethyl sulfate

~79%

alpha-methoxy-p-xylene Structure

alpha-methoxy-p...

Methyl 4-(methoxymethyl)benzoate Structure

Methyl 4-(metho...

~93%

4-(Methoxymethyl)-benzenemethanol Structure

4-(Methoxymethy...

4-(Methoxymethyl)benzoic acid Structure

4-(Methoxymethy...

~%

4-(Methoxymethyl)-benzenemethanol Structure

4-(Methoxymethy...

1,1-dimethylethyl 4-(methoxymethyl)benzoate Structure

1,1-dimethyleth...

~%

4-(Methoxymethyl)-benzenemethanol Structure

4-(Methoxymethy...

Benzyl acetate Structure

~%

Benzenemethanol,4-nitro-, 1-acetate Structure

Benzenemethanol...

3-Nitrobenzyl acetate Structure

3-Nitrobenzyl a...

2-nitrobenzyl acetate Structure

2-nitrobenzyl a...

4-(Methoxymethyl)-benzenemethanol Structure

4-(Methoxymethy...

~89%

4-(methoxymethyl)benzyl chloride Structure

4-(methoxymethy...

Methyl 4-(methoxymethyl)benzoate Structure

Methyl 4-(metho...

~%

4-(methoxymethyl)benzyl chloride Structure

4-(methoxymethy...

4-(Methoxymethyl)benzoic acid Structure

4-(Methoxymethy...

~%

4-(methoxymethyl)benzyl chloride Structure

4-(methoxymethy...

1,1-dimethylethyl 4-(methoxymethyl)benzoate Structure

1,1-dimethyleth...

~%

4-(methoxymethyl)benzyl chloride Structure

4-(methoxymethy...

1-Methoxy-3-(methoxymethyl)benzene Structure

1-Methoxy-3-(me...

~42%

m-Anisaldehyde Structure

1-(methoxymethyl)-3-methylbenzene Structure

1-(methoxymethy...

~88%

m-Tolualdehyde Structure

Methyl 4-(methoxymethyl)benzoate Structure

Methyl 4-(metho...

~88%

Methyl 4-formylbenzoate Structure

Methyl 4-formyl...

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