Sulfuric Acid → (5-Tert-butyl-4-hydroxy-2-methyl-phenyl)-acetic acid

HRID 23470Notes

Reaction equation

HRID 23470 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([CH3:12])[CH:3]=1.[C:13](O)([CH3:16])([CH3:15])[CH3:14].S(=O)(=O)(O)O>O>[C:13]([C:7]1[C:2]([OH:1])=[CH:3][C:4]([CH3:12])=[C:5]([CH2:8][C:9]([OH:11])=[O:10])[CH:6]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 139793582-(4-Hydroxy-2-methylphenyl)acetic acid

Product 1

HCID 22572841(5-Tert-butyl-4-hydroxy-2-methyl-phenyl)-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8.5 g (51 mmol) of (4-hydroxy-2-methyl-phenyl)-acetic acid (Indian J. Chem. Sect. B. 26, 1987:679-682), tert-butanol (60 g), and conc. sulfuric acid (2 mL) was stirred at 70° C. for 5 days. The solution was cooled to room temperature, poured into water, and extracted with EtOAc. The organic extract was washed with brine, dried (MgSO4), and concentrated to give (5-tert-butyl-4-hydroxy-2-methyl-phenyl)-acetic acid.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6207c329b2454f838776e751f16300c4
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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