Potassium Hydroxide → 2-(Hydroxymethyl)-5-methylbenzoic acid

HRID 2361332

Reaction equation

HRID 2361332 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[OH-:12].[K+]>CO.O>[OH:12][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:9]=1[C:8]([OH:7])=[O:11]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 6387566-Methylphthalide

Product 1

HCID 679628172-(Hydroxymethyl)-5-methylbenzoic acidYield 59.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A colorless, homogeneous solution of 6-methylisobenzofuran-1(3H)-one (0.95 g, 6.41 mmol), KOH (0.576 g, 10.26 mmol) in methanol (20.52 mL) and water (5.13 mL) was refluxed. After two hr, the reaction was cooled to room temperature, concentrated in vacuo, and acidified with 1 M aqueous KHSO4 to pH ˜3. The mixture was extracted with EtOAc (4×50 mL). The combined extract was dried over MgSO4 and concentrated in vacuo to give the desired product (0.632 g, 3.81 mmol, 59.4% yield) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe mixture was extracted with EtOAc (4×50 mL)
  3. extractionThe combined extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8707a0efd23f4914ba4fe44be75131be
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Linked notes

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