Potassium Hydroxide → 4-(Hydroxymethyl)-2-methoxybenzoic acid

HRID 1463838Notes

Reaction equation

HRID 1463838 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[C:5]([O:13][CH3:14])[CH:4]=1.[OH-:15].[K+]>O>[OH:15][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[C:5]([O:13][CH3:14])[CH:4]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11288398Methyl 4-(bromomethyl)-2-methoxybenzoate

Product 1

HCID 212548144-(Hydroxymethyl)-2-methoxybenzoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-bromomethyl-2-methoxybenzoate (25.0 g, 96.5 mmol), potassium hydroxide (10.83 g, 193 mmol) and water (400 mL) was refluxed with stirring for 2 hr. The reaction mixture was cooled, further basified to pH 14, and extracted three times with ethyl ether. The reaction solution was then acidified to pH 1 and extracted several times with ethyl acetate. The ethyl acetate layers were combined, dried (Na2SO4) and evaporated to yield 16.3 g (93%) of the title compound as an off white solid, m. pt 106-111°, whose purity was suitable for use without further purification. Additional purification is effected by recrystallization from ethyl acetate and hexane, m. pt, 112-115°.

Workup

  1. temperaturewas refluxed
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted three times with ethyl ether
  4. extractionextracted several times with ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-ea02ecf1e9934490baa97a0a241f137e
Source dataset
uspto-grants-1994_04
Patent number
US05302601

Reaction notes

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