Water → 3-Hydroxy-2-methylbenzoic Acid

HRID 1595980Notes

Reaction equation

HRID 1595980 reaction equation
C[C:2](C)([O-:4])C.[K+].C([OH:11])(C)(C)C.[OH2:12].[C:13]1([CH3:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[OH:12][C:14]1[C:13]([CH3:19])=[C:18]([CH:17]=[CH:16][CH:15]=1)[C:2]([OH:4])=[O:11]

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 6386tert-ButanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 2520233-Hydroxy-2-methylbenzoic AcidYield 79%

Procedure

The cycloadduct (1.05 g) from Example 2, 1.80 g of potassium tert-butoxide and 9 mL of tert-butanol were combined and refluxed a total of 9 hours. The reaction mixture was poured into water. Toluene was added. The toluene phase was washed twice with dilute sodium hydroxide solution. The combined aqueous phases were acidified with HCl, then extracted several times with t-butyl acetate. The n-butyl acetate was stripped, and the product dried in a vacuum oven to give 0.87 g of 3-hydroxy-2-methylbenzoic acid, 94% purity, 79% yield.

Workup

  1. temperaturerefluxed a total of 9 hours
  2. washThe toluene phase was washed twice with dilute sodium hydroxide solution
  3. extractionextracted several times with t-butyl acetate
  4. customthe product dried in a vacuum oven

Sources & evidence

ORD record
ord-15720bad53db46e0a92860ff242dc8c5
Source dataset
uspto-grants-2001_09
Patent number
US06288260B1

Reaction notes

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