Sodium Hydroxide → 3-tert-Butyl-4-hydroxybenzoic acid

HRID 257290Notes

Reaction equation

HRID 257290 reaction equation
C([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[C:14]([CH3:17])([CH3:16])[CH3:15])(=O)C.[OH-].[Na+]>CO.O>[C:14]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:5]=1[OH:4])[C:9]([OH:11])=[O:10])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 180077364-(Acetyloxy)-3-tert-butylbenzoic acid

Product 1

HCID 144015103-tert-Butyl-4-hydroxybenzoic acidYield 98.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

50.0 g of 4-acetoxy-3-tert-butylbenzoic acid are dissolved in 200 g of methanol. A solution of 10.2 g of sodium hydroxide in 180 ml of water is added. The mixture is refluxed for 3 hours. The methanol is removed, and the mixture is acidified with hydrochloric acid (10%) at 10° C. The precipitate is filtered off and washed, giving 40.6 g of product in the form of colourless crystals having a melting point of from 158° to 159° C.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. customThe methanol is removed
  3. customis acidified with hydrochloric acid (10%) at 10° C
  4. filtrationThe precipitate is filtered off
  5. washwashed

Sources & evidence

ORD record
ord-775757d1a73e4ed2b2ea09f52f98304c
Source dataset
uspto-grants-1993_11
Patent number
US05261953

Reaction notes

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