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

HRID 1589456Notes

Reaction equation

HRID 1589456 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 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. extractionextracted with benzene
  2. extractionthe benzene solution was extracted with dilute alkali
  3. additionthe obtained dilute alkali
  4. extractionextract
  5. extractionextracted with benzene
  6. customto remove impurities
  7. extractionextracted with benzene
  8. extractionThe benzene extract
  9. washwas washed with water
  10. dry with materialdried over Na2SO4
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-54463866957047b083e2336fc6f53999
Source dataset
uspto-grants-1986_02
Patent number
US04570005

Reaction notes

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