Potassium Carbonate → Dimethyl 4-(2-oxopropoxy)phenylmalonate

HRID 1901217

Reaction equation

HRID 1901217 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.Br[CH2:18][C:19](=[O:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:21]=[C:19]([CH3:20])[CH2:18][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 3018973Dimethyl (4-hydroxyphenyl)malonate

Product 1

HCID 21832135Dimethyl 4-(2-oxopropoxy)phenylmalonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following a procedure similar to that described in Preparation 3, but using 0.5 g of dimethyl 4-hydroxyphenylmalonate, 0.612 g of bromoacetone, 0.616 g of potassium carbonate and 90 ml of dimethylformamide, and then purifying the reaction product by column chromatography through silica gel, using a 2:3 by volume mixture of ethyl acetate and hexane as the eluent, the title compound was obtained having an Rf=0.37 (thin layer chromatography over silica gel, using a 2:3 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customthat described in Preparation 3
  2. custompurifying the reaction product by column chromatography through silica gel
  3. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-2e81623705854f4e80ce4dc9d1159da3
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Linked notes

Loading…