Water → Methyl 3-t-butyl-4-methoxy-5-methylsulfanylbenzoate

HRID 385102Notes

Reaction equation

HRID 385102 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([S:16][CH3:17])[C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].[C:18](=O)([O-])[O-].[K+].[K+].COS(=O)(=O)OC.O>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([S:16][CH3:17])[C:14]=1[O:15][CH3:18])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 86668170Methyl 3-t-butyl-4-hydroxy-5-methylsulfanylbenzoate

Product 1

HCID 68108649Methyl 3-t-butyl-4-methoxy-5-methylsulfanylbenzoateYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-t-butyl-4-hydroxy-5-methylsulfanylbenzoate (377 mg) was dissolved in N,N-dimethylformamide (7 mL), and potassium carbonate (818 mg) and dimethylsulfuric acid (0.32 mL) were added to the solution, and then the mixture was stirred at room temperature for 20 hours. Water was added to the reaction solution, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (344 mg) as a pale yellow oily substance.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cc17653a6d7e4ec2919e587a92ef8b37
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

Loading…