Sodium Hydroxide → 2-Fluoro-4-methoxybenzoic acid

HRID 858235Notes

Reaction equation

HRID 858235 reaction equation
[OH-:1].[Na+].[F:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]>O>[F:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:5]=1[C:6]([OH:1])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 27348732-Fluoro-4-methoxybenzaldehyde

Product 1

HCID 27745422-Fluoro-4-methoxybenzoic acidYield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a warm (55° C.) mixture of Ag2O (13.5 g, 58.4 mmol), NaOH (19.5 g, 487 mmol) and water (200 mL) was added 2-fluoro-4-methoxybenzaldehyde (15 g, 97.4 mmol). The mixture was stirred for 1 h, filtered off and the precipitated solids were washed with hot water (10 mL). The filtrate was added slowly into cold (0° C.) HCl (5N) with vigorous stirring. The precipitated solid was filtered, washed with water and dried to give a white solid (13.6 g, 82% yield, m.p. 194–196° C.); MS m/e 169 (M−H)+.

Workup

  1. temperatureInto a warm
  2. filtrationfiltered off
  3. washthe precipitated solids were washed with hot water (10 mL)
  4. additionThe filtrate was added slowly into cold (0° C.) HCl (5N) with vigorous stirring
  5. filtrationThe precipitated solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-6ab1f168f72d4bee92cc169c6547aeb1
Source dataset
uspto-grants-2006_12
Patent number
US07148247B2

Reaction notes

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