Potassium Carbonate → Benzyl 4-methoxycarbonylmethyloxyphenylacetate

HRID 581834Notes

Reaction equation

HRID 581834 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29][CH3:30])=[O:28]>CN(C)C=O>[CH3:30][O:29][C:27]([CH2:26][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])=[CH:6][CH:7]=1)=[O:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 11107524Benzyl 2-(4-hydroxyphenyl)acetate

Product 1

HCID 53972878Benzyl 4-methoxycarbonylmethyloxyphenylacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

After stirring a suspension of 8.4 g (0.035 mol) of benzyl 4-hydroxy-phenylacetate and 4.8 g (0.035 mol) of dried potassium carbonate in 100 ml of dimethylformamide at room temperature for 45 minutes, 5.3 g (0.038 mol) of methyl bromoacetate are slowly added and the mixture is then heated at 80° C. for 5 hours, with further stirring. Thereafter, stirring is continued overnight at room temperature. The solid is filtered off and the mother liquor is concentrated to dryness under reduced pressure. The residue is purified over a silica gel column, methylene chloride being used as the eluting agent.

Workup

  1. stirringThereafter, stirring
  2. filtrationThe solid is filtered off
  3. concentrationthe mother liquor is concentrated to dryness under reduced pressure
  4. customThe residue is purified over a silica gel column, methylene chloride being

Sources & evidence

ORD record
ord-f44e0533dca2460f9764e74d8f98c336
Source dataset
uspto-grants-1999_07
Patent number
US05922717

Reaction notes

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