Ethyl Acetate → HCID 14888727, compound

HRID 1647068Notes

Reaction equation

HRID 1647068 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C>C(O)=O>[CH2:1]([O:8][C:9](=[O:26])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 14888726HCID 14888726, compound

Product 1

HCID 14888727HCID 14888727, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1,1-dimethylethyl 3-[4-(2-benzyloxy-2-oxoethyl)phenyl]propanoate (3.0 g, 8.5 mmol) was stirred in formic acid (10 mL) for 8 hours. Removal of the solvent in vacuo provided a colorless oil that was shaken vigorously with a mixture of ethyl acetate and hexanes (1:3, 20 mL) until it solidified. The mixture was cooled in ice water and the product, collected by suction filtration to give 3-[4-(2-benzyloxy-2-oxoethyl)phenyl]propanoic acid, as a white solid (2.2 g, 7.4 mmol) in 87% yield, mp. 62°-64.5° C.

Workup

  1. customRemoval of the solvent in vacuo
  2. customprovided a colorless oil that
  3. filtrationthe product, collected by suction filtration

Sources & evidence

ORD record
ord-bb3b7246519249d5be2e1c9e13a32fb7
Source dataset
uspto-grants-1993_01
Patent number
US05182263

Reaction notes

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