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

HRID 866842Notes

Reaction equation

HRID 866842 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-4-cyclohexylcinnamate.

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-afa0074bc1394dcdbc2459207df2527b
Source dataset
uspto-grants-1978_07
Patent number
US04101591

Reaction notes

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