Water → Methyl 3,5-di-tert-butylbenzoate

HRID 37626Notes

Reaction equation

HRID 37626 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:13]=1)[C:8]([OH:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].IC.[C:20](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:2][C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:13]=1)[C:8]([O:10][CH3:20])=[O:9])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 853393,5-Bis(tert-butyl)benzoic acid

Product 1

HCID 13267559Methyl 3,5-di-tert-butylbenzoateYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.50 g (23.5 mmoles) of 3,5-di-t-butylbenzoic acid in 25 ml of dry dimethylformamide was added 5.01 g (35.3 mmoles) of iodomethane, and then 6.49 g of anhydrous potassium carbonate. After stirring at room temperature for 2 hours, water was added, the mixture was extracted three times with diethyl ether, the combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated to give 5.68 g of the title compound as a crystalline solid, m.p. 52.0°-52.5° C. The structural assignment was supported by 1H NMR.

Workup

  1. extractionthe mixture was extracted three times with diethyl ether
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-18c7bdf80cab41a8bc762755178fbc22
Source dataset
uspto-grants-1995_05
Patent number
US05420343

Reaction notes

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