P-Chloroacetophenone → (2E)-1-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one

HRID 1707056Notes

Reaction equation

HRID 1707056 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH:9]=[CH:13][N:14]([CH3:16])[CH3:15])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7467P-ChloroacetophenoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 605938(2E)-1-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one

Procedure

A mixture of 10.0 g. of p-chloroacetophenone and 25 ml. of dimethylformamide dimethylacetal is refluxed for 3 hours. Evaporation gives a thick oil which crystallized with the addition of hexane, to give the product, m.p. 78.5°-80.5° C. Recrystallization from methylene chloride and hexane provides the product of the Example as crystals, m.p. 83°-84° C.

Workup

  1. additionA mixture of 10.0 g
  2. customEvaporation
  3. customgives a thick oil which
  4. customcrystallized with the addition of hexane
  5. customto give the product, m.p. 78.5°-80.5° C
  6. customRecrystallization from methylene chloride and hexane
  7. customprovides the product of the Example as crystals, m.p. 83°-84° C.

Sources & evidence

ORD record
ord-5ff3719d4fb34faabf49173b8330b4f4
Source dataset
uspto-grants-1980_06
Patent number
US04209621

Reaction notes

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