Acetic Anhydride → HCID 136477422, compound

HRID 568715Notes

Reaction equation

HRID 568715 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1/[C:9](=[N:19]/[OH:20])/[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[OH:18].[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[C:21]([O:20]/[N:19]=[C:9](/[C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[F:1])\[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[OH:18])(=[O:23])[CH3:22]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 136477445HCID 136477445, compound

Product 1

HCID 136477422HCID 136477422, compoundYield 74.5%

Procedure

A mixture of 40 g of 2',5'-difluoro-2-hydroxy-4-methoxybenzophenone hydrochloride and 230 ml of pyridine is refluxed overnight. The pyridine is evaporated in vacuo. The residue is partitioned between 5% hydrochloric acid and ethyl acetate. The ethyl acetate solution is dried over anhydrous sodium sulfate and evaporated. The residue was triturated with hexane to give E-2',5'-difluoro-2-hydroxy-4-methoxybenzophenone oxime. A mixture of 35 g of the oxime and 25.6 g of acetic anhydride is placed in an oil bath at 60° C. for 45 min. The reaction mixture is partitioned between ether and sodium bicarbonate solution. The ether extract is dried over anhydrous sodium sulfate and evaporated. Recrystallization of the residue from 95% ethanol gives 30 g of E-2',5'-difluoro-2-hydroxy-4-methoxybenzophenone O-acetyl oxime, mp 110°-111° C.

Workup

  1. customThe reaction mixture is partitioned between ether and sodium bicarbonate solution
  2. extractionThe ether extract
  3. dry with materialis dried over anhydrous sodium sulfate
  4. customevaporated
  5. customRecrystallization of the residue from 95% ethanol

Sources & evidence

ORD record
ord-025f4827acf2471db2c154e1054fac5a
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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