4'-Chloropropiophenone → 4'-Chloro-3-dimethylamino-2-methylacrylophenone

HRID 231509

Reaction equation

HRID 231509 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:11])[C:9]([CH3:10])=[CH:14][N:15]([CH3:16])[CH3:17])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 226974'-ChloropropiophenoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 538154144'-Chloro-3-dimethylamino-2-methylacrylophenone

Procedure

A mixture of 50.0 g of p-chloropropiophenone and 200 ml of N,N-dimethylformamide dimethyl acetal was stirred and heated at reflux for 28 hours. The reaction mixture was evaporated in vacuo to give a yellow oil. The oil was then subjected to Kugelrohr distillation. The residual oil from the distillation was collected and triturated with hexane to provide crystals. The solid was collected by filtration and gave 21.5 g of 4'-chloro-3-dimethylamino-2-methylacrylophenone as yellow crystals, mp 45°-47° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 28 hours
  3. customThe reaction mixture was evaporated in vacuo
  4. customto give a yellow oil
  5. distillationThe oil was then subjected to Kugelrohr distillation
  6. distillationThe residual oil from the distillation
  7. customwas collected
  8. customtriturated with hexane
  9. customto provide crystals
  10. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-f46b79335d2345a3a60be1bf6ca49e28
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Linked notes

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