The preparation and diazotisation of some o- and p-aminophenyl benzoates and benzamides

S. Vickers; D. J. Triggle; D. R. Garrison

doi:10.1039/j39680000632

The preparation and diazotisation of some o- and p-aminophenyl benzoates and benzamides

S. Vickers
, D. J. Triggle
, D. R. Garrison

School of Pharmacy and Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

The preparation and diazotisation of some o- and p-aminophenyl benzoates and benzamides is described. On diazotisation, the 2,6-dimethylbenzoate of o-aminophenol is immediately and quantitatively hydrolysed to 2,6-dimethylbenzoic acid and o-hydroxybenzenediazonium chloride. In contrast, the 2,6-dichlorobenzoate of o-aminophenol diazotises normally as do the 2,6-dimethyl-, 4-methoxy-, and 2,6-dimethoxy-benzoates of p-aminophenol. Possible mechanisms for the hydrolytic diazotisation are described.

Original language	English
Pages (from-to)	632-634
Number of pages	3
Journal	Journal of the Chemical Society C: Organic Chemistry
DOIs	https://doi.org/10.1039/j39680000632
State	Published - 1968

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title = "The preparation and diazotisation of some o- and p-aminophenyl benzoates and benzamides",

abstract = "The preparation and diazotisation of some o- and p-aminophenyl benzoates and benzamides is described. On diazotisation, the 2,6-dimethylbenzoate of o-aminophenol is immediately and quantitatively hydrolysed to 2,6-dimethylbenzoic acid and o-hydroxybenzenediazonium chloride. In contrast, the 2,6-dichlorobenzoate of o-aminophenol diazotises normally as do the 2,6-dimethyl-, 4-methoxy-, and 2,6-dimethoxy-benzoates of p-aminophenol. Possible mechanisms for the hydrolytic diazotisation are described.",

author = "S. Vickers and Triggle, \{D. J.\} and Garrison, \{D. R.\}",

year = "1968",

doi = "10.1039/j39680000632",

language = "English",

pages = "632--634",

journal = "Journal of the Chemical Society C: Organic Chemistry",

issn = "0022-4952",

publisher = "Chemical Society",

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TY - JOUR

T1 - The preparation and diazotisation of some o- and p-aminophenyl benzoates and benzamides

AU - Vickers, S.

AU - Triggle, D. J.

AU - Garrison, D. R.

PY - 1968

Y1 - 1968

N2 - The preparation and diazotisation of some o- and p-aminophenyl benzoates and benzamides is described. On diazotisation, the 2,6-dimethylbenzoate of o-aminophenol is immediately and quantitatively hydrolysed to 2,6-dimethylbenzoic acid and o-hydroxybenzenediazonium chloride. In contrast, the 2,6-dichlorobenzoate of o-aminophenol diazotises normally as do the 2,6-dimethyl-, 4-methoxy-, and 2,6-dimethoxy-benzoates of p-aminophenol. Possible mechanisms for the hydrolytic diazotisation are described.

AB - The preparation and diazotisation of some o- and p-aminophenyl benzoates and benzamides is described. On diazotisation, the 2,6-dimethylbenzoate of o-aminophenol is immediately and quantitatively hydrolysed to 2,6-dimethylbenzoic acid and o-hydroxybenzenediazonium chloride. In contrast, the 2,6-dichlorobenzoate of o-aminophenol diazotises normally as do the 2,6-dimethyl-, 4-methoxy-, and 2,6-dimethoxy-benzoates of p-aminophenol. Possible mechanisms for the hydrolytic diazotisation are described.

UR - https://www.scopus.com/pages/publications/37049132587

U2 - 10.1039/j39680000632

DO - 10.1039/j39680000632

M3 - Article

AN - SCOPUS:37049132587

SN - 0022-4952

SP - 632

EP - 634

JO - Journal of the Chemical Society C: Organic Chemistry

JF - Journal of the Chemical Society C: Organic Chemistry

ER -

The preparation and diazotisation of some o- and p-aminophenyl benzoates and benzamides

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