p-Toluenesulfonic acid → 4-(1-Methoxy-1-methyl-ethyl)-benzoic acid methyl ester

HRID 395731Notes

Reaction equation

HRID 395731 reaction equation
[OH:1][C:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[C:15]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:15][O:1][C:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 18174533Methyl 4-(2-hydroxypropan-2-yl)benzoate

Product 1

HCID 181744854-(1-Methoxy-1-methyl-ethyl)-benzoic acid methyl esterYield 153.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(1-hydroxy-1-methylethyl)benzoate (340 mg, 1.75 mmol) in methanol (20 mL) was added p-toluenesulfonic acid (70 mg, 0.37 mmol). The mixture was refluxed for 48 h, concentrated in vacuo, and the residue chromatographed (silica gel, 10% ethyl acetate/90%hexanes to 30% ethyl acetate/70% hexanes) to give 118 mg (32%) of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 48 h
  2. concentrationconcentrated in vacuo
  3. customthe residue chromatographed (silica gel, 10% ethyl acetate/90%hexanes to 30% ethyl acetate/70% hexanes)

Sources & evidence

ORD record
ord-5fa0df9e217b44da8b029a148c7659b8
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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