Ethyl 4-hydroxyphenylacetate → HCID 14022788, compound

HRID 1957519Notes

Reaction equation

HRID 1957519 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH3:2]>CC[O-].[Na+].C(O)C.[Ni]>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH:6]1[CH2:7][CH2:8][CH:9]([OH:12])[CH2:10][CH2:11]1)[CH3:2]

Participants

5

Reactant 1

HCID 28310Ethyl 4-hydroxyphenylacetate

Product 1

HCID 14022788HCID 14022788, compoundYield 64.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 2723922Sodium ethoxideSolvent

Procedure

115 g 4-hydroxy-phenylacetic acid ethyl ester is hydrogenated in a mixture of 10 ml one molar sodium ethylate solution and 350 ml ethanol for 72 hours at 160° C. and 200 bar using Raney-Nickel. The preparation is subsequently evaporated and the remaining oil is distilled in a high vacuum. 76.4 g 4-hydroxycyclohexane-acetic acid ethyl ester is obtained with a boiling point of 120°-121° C./2 mm Hg. TLC (mobile solvent: dichloromethane/methanol 9:1). Rf=0.8.

Workup

  1. customThe preparation is subsequently evaporated
  2. distillationthe remaining oil is distilled in a high vacuum

Sources & evidence

ORD record
ord-eb4b245169544e9b9052e35f43b260e4
Source dataset
uspto-grants-1998_07
Patent number
US05786371

Reaction notes

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