Benzoyl chloride → 2-Benzoyloxyimino-2-(3-hydroxyphenyl)acetic acid

HRID 126752Notes

Reaction equation

HRID 126752 reaction equation
[OH:1][N:2]=[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)[C:4]([OH:6])=[O:5].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[C:14]([O:1][N:2]=[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)[C:4]([OH:6])=[O:5])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 867363792-Hydroxyimino-2-(3-hydroxyphenyl)acetic acid

Product 1

HCID 537831312-Benzoyloxyimino-2-(3-hydroxyphenyl)acetic acidYield 77.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-hydroxyimino-2-(3-hydroxyphenyl)acetic acid (syn isomer) (9.06 g.), benzoyl chloride (32.25 g.) and tetrahydrofuran (50 ml.) was stirred for 6 hours at ambient temperature. To the reaction mixture was added petroleum ether under 5° C. Precipitates were collected by filtration, washed with petroleum ether and dried to give 2-benzoyloxyimino-2-(3-hydroxyphenyl)acetic acid (syn isomer) (11.12 g.), mp 140° to 142° C. (dec.).

Workup

  1. customPrecipitates
  2. filtrationwere collected by filtration
  3. washwashed with petroleum ether
  4. customdried

Sources & evidence

ORD record
ord-98df32b6badb47dca13005bc92449468
Source dataset
uspto-grants-1981_03
Patent number
US04254117

Reaction notes

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