Acetic Acid → 1,5-Diethyl 2-(4-cyclohexylphenyl)pentanedioate

HRID 917918Notes

Reaction equation

HRID 917918 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)[CH3:2].[CH2:19]([O:21][C:22](=[O:25])[CH:23]=[CH2:24])[CH3:20].[Na].C(O)(=O)C>C(O)C.O>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:10][CH:11]=1)[CH2:24][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:25])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 5360545SodiumHCID 53423226Ethyl (4-cyclohexylphenyl)acetate

Product 1

HCID 539609881,5-Diethyl 2-(4-cyclohexylphenyl)pentanedioate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 15 g of para-cyclohexyl-phenylacetic acid ethyl ester and 6.7 g of acrylic acid ethyl ester is added dropwise to a solution of 1.5 g of sodium in 25 ml of ethanol. The solution is boiled overnight and then poured into a mixture of 5 ml of glacial acetic acid and 75 ml of water. The alcohol is distilled off and the batch extracted with ethyl acetate. The residue remaining on evaporation of the ethyl acetate is distilled in a high vacuum. There is obtained 2-(para-cyclohexylphenyl)-glutaric acid diethyl ester boiling at 184°-186°C under a pressure of 0.4 mm of Hg.

Workup

  1. distillationThe alcohol is distilled off
  2. extractionthe batch extracted with ethyl acetate
  3. customThe residue remaining on evaporation of the ethyl acetate
  4. distillationis distilled in a high vacuum

Sources & evidence

ORD record
ord-b2716debf7494e5692caff65a51a6a42
Source dataset
uspto-grants-1976_07
Patent number
US03968142

Reaction notes

Loading…