4'-Methoxyacetophenone → 3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one

HRID 1707058Notes

Reaction equation

HRID 1707058 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[CH3:14][N:15]([CH3:17])[CH:16]=[CH:10][C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:11]

Participants

3

Reactant 2

HCID 74764'-MethoxyacetophenoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 7224023-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one

Procedure

A mixture of 25 g. of p-methoxyacetophenone and 25 ml. of dimethylformamide dimethylacetal is refluxed for 9 hours. Evaporation gives an oil which crystallized on the addition of hexane. Recrystallization from methylene chloride and hexane gives the desired compound, m.p. 92°-95° C.

Workup

  1. additionA mixture of 25 g
  2. customEvaporation
  3. customgives an oil which
  4. customcrystallized on the addition of hexane
  5. customRecrystallization from methylene chloride and hexane

Sources & evidence

ORD record
ord-76fb4e6b26464811b9cbda1ab5e7fe4f
Source dataset
uspto-grants-1980_06
Patent number
US04209621

Reaction notes

Loading…