Ethanol → Ethyl 3-(3-chloro-4-cyclohexylphenyl)prop-2-enoate

HRID 616751Notes

Reaction equation

HRID 616751 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:5]=[CH:6][C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH2:24](O)[CH3:25]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:5]=[CH:6][C:7]([O:9][CH2:24][CH3:25])=[O:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 542933553-Chloro-4-cyclohexylcinnamic acid

Product 1

HCID 53804855Ethyl 3-(3-chloro-4-cyclohexylphenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloro-4-cyclohexylcinnamic acid (20.0 g.; 0.075 moles) is allowed to reflux with 8-10 pieces of Orierite in absolute ethanol (20 ml) containing concentrated sulfuric acid (5 ml) for 21 hours. The cooled reaction mixture is diluted with chloroform and filtered hot. The filtrate is washed 3 times with water, once with 10% sodium bicarbonate and twice more with water. After dryng over sodium sulfate, the solvent is removed to give ethyl 3-chloro-4-cyclohexylcinnamate.

Workup

  1. customThe cooled reaction mixture
  2. filtrationfiltered hot
  3. washThe filtrate is washed 3 times with water
  4. customthe solvent is removed

Sources & evidence

ORD record
ord-9b3551a006e04832846ffe50a08610e6
Source dataset
uspto-grants-1978_02
Patent number
US04075354

Reaction notes

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