Water → 2-(4-Fluorophenyl)-2-methylbutanoic acid

HRID 434540Notes

Reaction equation

HRID 434540 reaction equation
[CH2:1]([C:3]([C:12]#N)([CH3:11])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)[CH3:2].S(=O)(=O)(O)[OH:15].[OH2:19]>>[F:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([CH3:11])([CH2:1][CH3:2])[C:12]([OH:15])=[O:19])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 13199826alpha-Ethyl-alpha-methyl-4-fluorobenzyl cyanide

Product 1

HCID 137117812-(4-Fluorophenyl)-2-methylbutanoic acid

Procedure

7.6 g of crude α-ethyl-α-methyl-4-fluorobenzyl cyanide, 20 ml of H2O and 20 ml of concentrated sulfuric acid were and refluxed at 134° to 137° C. for 5.5 hours. The mixture was cooled to room temperature and extracted with benzene, and the benzene solution was extracted with dilute alkali and the obtained dilute alkali extract was adjusted to pH 7.5 with concentrated hydrochloric acid, and extracted with benzene to remove impurities. Then, the aqueous solution was adjusted to pH 4.6 with concentrated hydrochloric acid and extracted with benzene. The benzene extract was washed with water, dried over Na2SO4, and evaporated under reduced pressure to give 3.8 g of 2-(4-fluorophenyl)-2-methylbutyric acid.

Workup

  1. temperaturerefluxed at 134° to 137° C. for 5.5 hours
  2. extractionextracted with benzene
  3. extractionthe benzene solution was extracted with dilute alkali
  4. additionthe obtained dilute alkali
  5. extractionextract
  6. extractionextracted with benzene
  7. customto remove impurities
  8. extractionextracted with benzene
  9. extractionThe benzene extract
  10. washwas washed with water
  11. dry with materialdried over Na2SO4
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-23813e63cb75477c8aa79949e399ca01
Source dataset
uspto-grants-1983_08
Patent number
US04397864

Reaction notes

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