Acetic Anhydride → [(E)-[(2-fluorophenyl)-(2-hydroxy-4-methoxy-3-methylphenyl)methylidene]amino] acetate

HRID 568653Notes

Reaction equation

HRID 568653 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[C:8](=[N:19]/[OH:20])/[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH3:17])[C:10]=1[OH:18].[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[C:21]([O:20]/[N:19]=[C:8](/[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])\[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH3:17])[C:10]=1[OH:18])(=[O:23])[CH3:22]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 1364773806-[(E)-C-(2-fluorophenyl)-N-hydroxycarbonimidoyl]-3-methoxy-2-methylphenol

Product 1

HCID 136477425[(E)-[(2-fluorophenyl)-(2-hydroxy-4-methoxy-3-methylphenyl)methylidene]amino] acetate

Procedure

E-2'-fluoro-2-hydroxy-4-methoxy-3-methylbenzophenone oxime (20.0 g) is warmed on a steam bath for one hour with 12 ml of acetic anhydride. The acetic anhydride is evaporated in vacuo and the product is distributed between ether and H2O, then the ether is washed with 10% NaHCO3. Evaporation and trituration of the crystalline product with hexane gives E-2'-fluoro-2-hydroxy-4-methoxy-3-methylbenzophenone O-acetyl oxime, mp 83°-86° C.

Workup

  1. customThe acetic anhydride is evaporated in vacuo
  2. washthe ether is washed with 10% NaHCO3
  3. customEvaporation and trituration of the crystalline product with hexane

Sources & evidence

ORD record
ord-2e8b5378bfc5468e9c3eb536d0f619c3
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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