Water → Methyl 3-t-butyl-5-iodo-4-methoxybenzoate

HRID 385031Notes

Reaction equation

HRID 385031 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([I:16])[C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].[C:17](=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]([I:16])[C:14]=1[O:15][CH3:17])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 12084815Methyl 3-t-butyl-4-hydroxy-5-iodobenzoate

Product 1

HCID 68108746Methyl 3-t-butyl-5-iodo-4-methoxybenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-t-butyl-4-hydroxy-5-iodobenzoate (2.77 g) was dissolved in N,N-dimethylformamide (50 mL), and potassium carbonate (12.0 g) and dimethylsulfuric acid (4.1 mL) were added to the solution, and then the mixture was stirred at room temperature for 16 hours. Water was added to the reaction solution, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (2.77 g) as a brown crystal.

Workup

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

Sources & evidence

ORD record
ord-a3fdc6c5d6c8440d9f6023c43467b14b
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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