Methanol → 4-Fluoro-2-methylbenzoic acid

HRID 2427486Notes

Reaction equation

HRID 2427486 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].[Na+].C[OH: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

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 38260554-Fluoro-2-methylbenzonitrile

Product 1

HCID 38606394-Fluoro-2-methylbenzoic acid

Procedure

4-Fluoro-2-methylbenzonitrile (2.9 g), 5N NaOH (50 mL), and MeOH (50 mL) were set stirring at 100° C. for 18 hours. The solvent was removed under reduced pressure and the product was washed with CH2Cl2 and acidified to pH 1. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2SO4 to yield a while solid (1.6 g). 1H NMR (300 MHz, CDCl3): δ 8.07-8.14 (m, 1H), 6.96-7.01 (m, 1H), 6.79-6.82 (m, 1H), 2.73 (br s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe product was washed with CH2Cl2
  3. customThe reaction was partitioned between ethyl acetate and water
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-76e86967165d481582c8e2e7489872ed
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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