Water → Methyl 3-tert-butyl-4-methoxybenzoate

HRID 2225161Notes

Reaction equation

HRID 2225161 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1O)[C:8]([OH:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].S([O:20][CH3:21])(OC)(=O)=O.[C:22](=O)([O-])[O-].[K+].[K+].O>C(C(C)=O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:20][CH3:21])[C:8]([O:10][CH3:22])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 144015103-tert-Butyl-4-hydroxybenzoic acid

Product 1

HCID 10775404Methyl 3-tert-butyl-4-methoxybenzoateYield 97.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

Preparation C11, Step 1: 3-tert-butyl-4-hydroxybenzoic acid (1.00 g, 5.15 mmol, 1 eq), dimethyl sulfate (1.07 mL, 11.3 mmol, 2.2 eq) and potassium carbonate (2.85 g, 20.6 mmol, 4 eq) were refluxed in methyl ethyl ketone (20 mL) for 3 hours. Worked up by adding H2O (20 mL) then stripped off the methyl ethyl ketone. The aqueous was extracted 3 times with diethyl ether (25 mL). The organic layers were combined, dried (sodium sulfate) and stripped to give methyl 3-tert-butyl-4-methoxybenzoate (1.12 g) of an amber oil Yield=97%. LCMS detects (M+H)+=223.23.

Workup

  1. customPreparation C11, Step 1
  2. extractionThe aqueous was extracted 3 times with diethyl ether (25 mL)
  3. dry with materialdried (sodium sulfate)

Sources & evidence

ORD record
ord-1542be9a5c264068932ac41ac1bd1acc
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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