P-Chloroacetophenone → 1-(4-Chlorophenyl)-3-(dimethylamino)but-2-en-1-one

HRID 231506Notes

Reaction equation

HRID 231506 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1)=[O:3].CO[C:13](OC)([N:15]([CH3:17])[CH3:16])[CH3:14]>>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH:1]=[C:13]([N:15]([CH3:17])[CH3:16])[CH3:14])=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 7467P-ChloroacetophenoneHCID 878351,1-Dimethoxyethyl(dimethyl)amine

Product 1

HCID 533959431-(4-Chlorophenyl)-3-(dimethylamino)but-2-en-1-one

Procedure

A mixture of 25.0 g of 4-chloroacetophenone and 40 ml of N,N-dimethylacetamide dimethyl acetal was stirred and heated at reflux for 3 hours. The mixture was evaporated in vacuo to give a red solid. The solid was triturated with n-hexane and filtered. The solid was washed with n-hexane and dried to give 15.6 g of 1-(4-chlorophenyl)-3-(dimethylamino)-2-buten-1-one as red crystals, mp 103°-105° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. customThe mixture was evaporated in vacuo
  4. customto give a red solid
  5. customThe solid was triturated with n-hexane
  6. filtrationfiltered
  7. washThe solid was washed with n-hexane
  8. customdried

Sources & evidence

ORD record
ord-92cdc2343164465190abb521f478ae24
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Reaction notes

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