Acetyl chloride → 2-Methoxyimino-2-(3-acetoxyphenyl)acetic acid

HRID 1447259Notes

Reaction equation

HRID 1447259 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][N:7]=[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1)[C:9]([OH:11])=[O:10]>N1C=CC=CC=1>[CH3:5][O:6][N:7]=[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:1](=[O:3])[CH3:2])[CH:13]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 543905512-Methoxyimino-2-(3-hydroxyphenyl)acetic acid

Product 1

HCID 537578682-Methoxyimino-2-(3-acetoxyphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetyl chloride (4.1 g.) was added with stirring and ice-cooling to a solution of 2-methoxyimino-2-(3-hydroxyphenyl)acetic acid (syn isomer) (5g.) in pyridine (20 ml.) and the mixture was stirred for 50 minutes at ambient temperature. The reaction mixture was poured into ice-water, adjusted to pH 2.1 and extracted three times with ether. The extract was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was thoroughly removed under reduced pressure to give 2-methoxyimino-2-(3-acetoxyphenyl)acetic acid (syn isomer) (6.1 g.).

Workup

  1. stirringthe mixture was stirred for 50 minutes at ambient temperature
  2. extractionextracted three times with ether
  3. washThe extract was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was thoroughly removed under reduced pressure

Sources & evidence

ORD record
ord-54c143abdf854be0a4d93470e34f3332
Source dataset
uspto-grants-1982_02
Patent number
US04316019

Reaction notes

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