Ethanol → Ethyl 3-(3-(trifluoromethyl)phenyl)propanoate

HRID 1389178Notes

Reaction equation

HRID 1389178 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1.S(=O)(=O)(O)O.O.[CH2:22](O)[CH3:23]>>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:22][CH3:23])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 27776833-(3-Trifluoromethylphenyl)propanoic acid

Product 1

HCID 11849913Ethyl 3-(3-(trifluoromethyl)phenyl)propanoate

Procedure

A solution of 3-(3-trifluoromethylphenyl)propionic acid (13.6 g) in anhydrous ethanol (25 ml) containing concentrated sulphuric acid (1.5 ml) was heated at reflux for 24 hours and was then poured into water (100 ml). The mixture was extracted with diethyl ether and the ethereal extract was washed with water, with aqueous sodium carbonate solution (2 N), and with water, then dried over magnesium sulphate and evaporated. The resulting residue was distilled, to give ethyl 3-(3-trifluoromethylphenyl)propionate (11.5 g) in the form of a colourless oil, b.p. 133°-135° C./17 mm Hg. [elemental analysis: C, 58.6; H, 5.2%. C12H13F3O2 requires C, 58.5; H, 5.3%. νmax 1125, 1170, 1330 and 1740 cm-1 ].

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. extractionThe mixture was extracted with diethyl ether
  4. extractionthe ethereal extract
  5. washwas washed with water, with aqueous sodium carbonate solution (2 N)
  6. dry with materialwith water, then dried over magnesium sulphate
  7. customevaporated
  8. distillationThe resulting residue was distilled

Sources & evidence

ORD record
ord-6aaab0cd6b5845118555448361df9825
Source dataset
uspto-grants-1981_01
Patent number
US04243683

Reaction notes

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