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

HRID 26563Notes

Reaction equation

HRID 26563 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 drying over sodium sulfate, the solvent is removed to give ethyl 3-chloro-4cyclohexylcinnamate.

Workup

  1. customThe cooled reaction mixture
  2. filtrationfiltered hot
  3. washThe filtrate is washed 3 times with water
  4. dry with materialAfter drying over sodium sulfate
  5. customthe solvent is removed

Sources & evidence

ORD record
ord-5ea96170c0154bb29ae01d0e1a9a2fdd
Source dataset
uspto-grants-1979_04
Patent number
US04150148

Reaction notes

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