Sulfuric Acid → p-Isobutylphenylacetic acid-2,2,2-trifluoroethyl ester

HRID 26461Notes

Reaction equation

HRID 26461 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#N)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[F:14][C:15]([F:19])([F:18])[CH2:16][OH:17].S(=O)(=O)(O)[OH:21]>>[F:14][C:15]([F:19])([F:18])[CH2:16][O:17][C:12](=[O:21])[CH2:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 64092,2,2-TrifluoroethanolHCID 170426(4-Isobutylphenyl)acetonitrile

Product 1

HCID 21323305p-Isobutylphenylacetic acid-2,2,2-trifluoroethyl esterYield 51.1%

Procedure

A mixture of 1.73 g of 4-isobutylphenylacetonitrile and 10 g of 95% of 2,2,2-trifluoroethanol and 10 g of concentrated sulfuric acid were refluxed for 12 hours. After the reaction was complete, ice-water was added to the mixture. The resulting mixture was extracted with ether. The ether layer separated was dehydrated and concentrated to leave an oily residue. The residue was distilled in vacuo to give 1.4 g of 4-isobutylphenylacetic acid-2,2,2-trifluoroethyl ester as a pale yellow oil, boiling at 77°-79° C./1 mmHg. Analysis-Calculated for C14H17F3O2 : C, 61.30; H, 6.25. Found: C, 61.21; H, 6.23.

Workup

  1. temperaturewere refluxed for 12 hours
  2. extractionThe resulting mixture was extracted with ether
  3. customThe ether layer separated
  4. concentrationconcentrated
  5. customto leave an oily residue
  6. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-8c1a8cb85b514d158b26466e15a975ed
Source dataset
uspto-grants-1979_04
Patent number
US04150137

Reaction notes

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