Acetic Acid → HCID 54511550, compound

HRID 917920Notes

Reaction equation

HRID 917920 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]([CH2:15][C:16]#[N:17])[CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[CH2:18]([O:20][C:21](=[O:24])[CH:22]=[CH2:23])[CH3:19].C(O)(=O)C>C(O)C.O>[CH2:18]([O:20][C:21](=[O:24])[CH2:22][CH2:23][CH:15]([C:5]1[CH:6]=[CH:7][C:8]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:3]([Cl:2])[CH:4]=1)[C:16]#[N:17])[CH3:19]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 5360545SodiumHCID 21524243HCID 21524243, compound

Product 1

HCID 54511550HCID 54511550, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2.5 g of sodium in 50 ml of ethanol there is added dropwise a mixture of 23.4 g of 3-chloro-4-cyclohexyl-phenylacetonitrile and 10 g of acrylic acid ethyl ester. The solution is boiled overnight and then poured into a mixture of 10 ml of glacial acetic acid and 150 ml of water. The ethanol is evaporated and the residue distilled in a high vacuum to obtain 4-(3-chloro-4-cyclohexylphenyl)-4-cyano-butyric acid ethyl ester boiling at 200°-203°C under a pressure of 0.35 mm of Hg.

Workup

  1. customThe ethanol is evaporated
  2. distillationthe residue distilled in a high vacuum

Sources & evidence

ORD record
ord-d952b743fddf46549262ddd702df1630
Source dataset
uspto-grants-1976_07
Patent number
US03968142

Reaction notes

Loading…