Dimethylformamide → Methyl 4-(2-oxopropoxy)cinnamate

HRID 1901193Notes

Reaction equation

HRID 1901193 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.Br[CH2:15][C:16](=[O:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[O:18]=[C:16]([CH3:17])[CH2:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 92203Methyl p-coumarate

Product 1

HCID 53842536Methyl 4-(2-oxopropoxy)cinnamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following a procedure similar to that described in Preparation 3, but using 16 g of methyl 4-hydroxycinnamate, 14.9 g of bromoacetone, 20 g of potassium carbonate and 150 ml of dimethylformamide, the title compound was obtained as crystals, melting at 117°-118° C. (after recrystallization from ethyl acetate).

Workup

  1. customthat described in Preparation 3

Sources & evidence

ORD record
ord-aa097d1100954820b7012c072269e532
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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