1-Octanol → Octyl [3-(trifluoromethyl)phenyl]acetate

HRID 1709005Notes

Reaction equation

HRID 1709005 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH2:15](O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 9571-OctanolHCID 6101p-Toluenesulfonic acidHCID 676953-(Trifluoromethyl)benzeneacetic acid

Product 1

HCID 13302037Octyl [3-(trifluoromethyl)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-trifluoromethylphenylacetic acid (150.0 g), n-octanol (130.0 g), p-toluenesulphonic acid (9.5 g) and benzene (800 ml) is refluxed for 7 hours with a Dean-Stark separator. The solution is washed with a 10% aqueous solution of sodium carbonate (3×500 ml) and with water (3×500 ml). After drying over magnesium sulphate, the solvent is evaporated in vacuo. The residue is distilled (95°-97°/2.10-2Torr) to yield n-octyl 3-trifluoromethylphenylacetate.

Workup

  1. temperatureis refluxed for 7 hours with a Dean-Stark separator
  2. washThe solution is washed with a 10% aqueous solution of sodium carbonate (3×500 ml) and with water (3×500 ml)
  3. dry with materialAfter drying over magnesium sulphate
  4. customthe solvent is evaporated in vacuo
  5. distillationThe residue is distilled (95°-97°/2.10-2Torr)

Sources & evidence

ORD record
ord-29da05df62fd42f69000922a6cf0b86e
Source dataset
uspto-grants-1990_08
Patent number
US04946861

Reaction notes

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