Hydrochloric Acid → 4-Fluoro-2-methylbenzoic acid

HRID 749464Notes

Reaction equation

HRID 749464 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[C:4]([CH3:10])[CH:3]=1.[OH-:11].[K+].Cl.[OH2:14]>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([OH:14])=[O:11])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 38260554-Fluoro-2-methylbenzonitrile

Product 1

HCID 38606394-Fluoro-2-methylbenzoic acidYield 92%

Procedure

A mixture of 4-fluoro-2-methylbenzonitrile (19.8 g, 150 mmol), KOH (24.3 g, 380 mmol) and water (300 mL) was heated to reflux for two days. The mixture was then acidified with concentrated HCl while cooling. The product was collected by filtration and the filter cake was washed with water. The solid material was dried standing in the hood for several days. There was obtained 20.8 g (92%) of 4-fluoro-2-methylbenzoic acid as a solid material. 1H NMR (300 MHz, DMSO-d6): 2.5 (s, 3H), 7.0-7.2 (m, 2H), 7.9 (t, 1H), 12.8 (b, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for two days
  3. temperaturewhile cooling
  4. filtrationThe product was collected by filtration
  5. washthe filter cake was washed with water
  6. customThe solid material was dried
  7. waitstanding in the hood for several days

Sources & evidence

ORD record
ord-eed52613de8049018d64ffaf7a161d77
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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