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

HRID 1380944Notes

Reaction equation

HRID 1380944 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 (1978)) 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. temperatureis heated
  2. temperatureto reflux for 24 hours
  3. concentrationThe solution is concentrated
  4. temperaturecooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-770d4bc732f3484e93d74e60cade809d
Source dataset
uspto-grants-1986_04
Patent number
US04584313

Reaction notes

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