Ethanol → Ethyl 3-[4-(trifluoromethyl)phenyl]prop-2-enoate

HRID 464732Notes

Reaction equation

HRID 464732 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[CH2:21]([O:10][C:9](=[O:11])[CH:8]=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:13][CH:12]=1)[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 749403-[4-(Trifluoromethyl)phenyl]prop-2-enoic acid

Product 1

HCID 53662772Ethyl 3-[4-(trifluoromethyl)phenyl]prop-2-enoate

Procedure

A suspension of 300 g of 4-trifluoromethylcinnamic acid (J. Org. Chem. 43:980 (1980) and 25 ml of concentrated sulfuric acid in 1.7 liters of ethanol is heated to reflux for 24 hours. The solution is concentrated, cooled, and filtered to give as a white solid, 4-trifluoromethylcinnamic acid ethyl ester, mp 40°-41° C.

Workup

  1. temperatureto reflux for 24 hours
  2. concentrationThe solution is concentrated
  3. temperaturecooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-6567a72a4b3e4ae7b82fada4fd7b010b
Source dataset
uspto-grants-1985_10
Patent number
US04548947

Reaction notes

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