Acetic Acid → HCID 53865942, compound

HRID 917911Notes

Reaction equation

HRID 917911 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[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)=[C:8]([Cl:18])[CH:7]=1)[CH3:2].[CH2:20]([O:22][C:23](=[O:26])[CH:24]=[CH2:25])[CH3:21].[Na].C(O)(=O)C>C(O)C>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)=[C:8]([Cl:18])[CH:7]=1)[CH2:25][CH2:24][C:23]([O:22][CH2:20][CH3:21])=[O:26])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 5360545SodiumHCID 54432300HCID 54432300, compound

Product 1

HCID 53865942HCID 53865942, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 40.5 g of 3-chloro-4-cyclohexylphenylacetic acid ethyl ester and 16 g of acrylic acid ethyl ester is added dropwise to a solution of 3.6 g of sodium in 60 ml of ethanol. The solution is refluxed overnight and then poured into a mixture of 10 ml of glacial acetic acid and 170 ml of ice water. The ethanol is distilled off and the residue extracted with ethyl acetate and evaporated; the residue is distilled under a high vacuum, to yield 24.3 g of 2-(3-chloro-4-cyclohexylphenyl)-glutaric acid diethyl ester boiling at 203°-205°C under 0.4 mm Hg pressure.

Workup

  1. temperatureThe solution is refluxed overnight
  2. distillationThe ethanol is distilled off
  3. extractionthe residue extracted with ethyl acetate
  4. customevaporated
  5. distillationthe residue is distilled under a high vacuum

Sources & evidence

ORD record
ord-938c01a54ee64754bd7a692a36c293ef
Source dataset
uspto-grants-1976_07
Patent number
US03968142

Reaction notes

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