Phenylacetone → 3-Buten-2-one, 4-(dimethylamino)-3-phenyl-

HRID 1980332Notes

Reaction equation

HRID 1980332 reaction equation
[C:1]1([CH2:7][C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[CH3:13][N:14]([CH3:16])[CH:15]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8](=[O:10])[CH3:9]

Participants

3

Reactant 2

HCID 7678PhenylacetoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 14883693-Buten-2-one, 4-(dimethylamino)-3-phenyl-

Procedure

A mixture of phenylacetone (13.4 grams) and dimethylformamide dimethylacetal (13.0 grams) was heated at 90°-95° C. on a steam bath for about 21/2 hours. A crude oil was produced which was then chromatographed on 600 ml of silica gel using ethyl acetate as an eluent. The final product, whose structure was confirmed by NMR, was a yellow oil which crystallized upon standing, yield 15.5 grams.

Workup

  1. temperaturewas heated at 90°-95° C. on a steam bath for about 21/2 hours
  2. customA crude oil was produced which
  3. customwas then chromatographed on 600 ml of silica gel
  4. customcrystallized

Sources & evidence

ORD record
ord-2e46054056c54f1bae0d88d5c93f87ae
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

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