Methanol → 4-Fluoro-2-methylbenzoic acid

HRID 2167357Notes

Reaction equation

HRID 2167357 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=[O:7])=[C:4](OC)[CH:3]=1.[OH-].[Na+].[CH3:15]O>>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:15])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 7020923HCID 7020923, compound

Product 1

HCID 38606394-Fluoro-2-methylbenzoic acidYield 85%

Procedure

To a solution of 4-fluoro-2-methoxybenzoate (10.0 g, 58.8 mmol) in methanol (50 mL) was slowly added 6 M NaOH solution (30 mL). White solid immediately precipitated and the mixture was stirred for another hour at room temperature before it was re-dissolved in H2O and acidified with 6 M HCl solution until precipitation occurred. The white solid was collected by vacuum filtration and dried on vacuum oven overnight to afford 4-fluoro-2-methyl benzoic acid (44, 9.2 g, 85%) 1H NMR (300 MHz, CDCl3) δ 8.21 (dd, J=9.0 Hz, 6.9 Hz, 1H), 6.82-6.88 (m, 1H), 6.79 (dd, J=7.8 Hz, 2.1 Hz, 1H), 4.07 (s, 1H).

Workup

  1. customWhite solid immediately precipitated
  2. dissolutionwas re-dissolved in H2O
  3. customacidified with 6 M HCl solution until precipitation
  4. filtrationThe white solid was collected by vacuum filtration
  5. customdried on vacuum oven overnight

Sources & evidence

ORD record
ord-dad4f67a6c624d19a1fef2e5a456a45c
Source dataset
uspto-grants-2015_06
Patent number
US09045445B2

Reaction notes

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