Potassium Carbonate → Benzyl 4-methoxycarbonylmethyloxyphenylacetate

HRID 1940524Notes

Reaction equation

HRID 1940524 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+].[CH3:25][O:26][C:27](=[O:30])[CH2:28]Br>CN(C)C=O>[CH3:25][O:26][C:27]([CH2:28][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:30]

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

Procedure

To a suspension of 8.4 g (0.035 Mol) of benzyl 4-hydroxyphenylacetate and 4.8 g (0.035 Mol) of dried potassium carbonate in 100 ml of dimethylformamide are added slowly, after 45 minutes stirring at ambient temperature, 5.3 g (0.038 Mol) of methylbromoacetate and the mixture is then heated to 80° C. for 5 minutes whilst stirring continues. It is then stirred overnight at ambient temperature. The solid matter is filtered off and the mother liquor is evaporated to dryness under reduced pressure. The residue is purified over a silica gel column, using methylene chloride as eluant. Yield: 7.9 g amorphous solid (72.9% of theory).

Workup

  1. additionare added slowly, after 45 minutes
  2. stirringwhilst stirring
  3. stirringIt is then stirred overnight at ambient temperature
  4. filtrationThe solid matter is filtered off
  5. customthe mother liquor is evaporated to dryness under reduced pressure
  6. customThe residue is purified over a silica gel column

Sources & evidence

ORD record
ord-b89f86951dee4782b9c93b1d458a2297
Source dataset
uspto-grants-1997_12
Patent number
US05700801

Reaction notes

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