P-Chloroacetophenone → HCID 15338017, compound

HRID 964914Notes

Reaction equation

HRID 964914 reaction equation
[Cl:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1>CCOCC>[Cl:1][C:2]([F:8])([F:9])[C:3](=[O:5])[CH2:21][C:20]([C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=1)=[O:22]

Participants

5

Reactant 3

HCID 7467P-ChloroacetophenoneHCID 67843Acetic acid, 2-chloro-2,2-difluoro-, ethyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 15338017HCID 15338017, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

38 g of ethyl chlorodifluoroacetate was added to 22.7 g of sodium methoxide and 300 ml of dry ether under cooling with ice. 31 g of p-chloroacetophenone was gradually added thereto under cooling with ice. The mixture was stirred at room temperature for 12 hours. The solvent was distilled off. 150 ml of 6N hydrochloric acid was added under cooling with ice, and extraction with ethyl acetate was carried out. The extract layer was washed with water, and the solvent was distilled off. The resulting crude product was purified by silica gel column chromatography (developing solvent: chloroform), and thereby 49.5 g of the desired product was obtained as a pale yellow viscous liquid. m.p. 50°-51° C.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. distillationThe solvent was distilled off
  4. addition150 ml of 6N hydrochloric acid was added
  5. temperatureunder cooling with ice, and extraction with ethyl acetate
  6. washThe extract layer was washed with water
  7. distillationthe solvent was distilled off
  8. customThe resulting crude product was purified by silica gel column chromatography (developing solvent: chloroform)

Sources & evidence

ORD record
ord-88dd58538f20473d98d45e69d9e2e91e
Source dataset
uspto-grants-1998_06
Patent number
US05773388

Reaction notes

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