Methyl iodide → Methyl 3-(benzyloxy)-5-methoxybenzoate

HRID 38655Notes

Reaction equation

HRID 38655 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([OH:19])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoate

Product 1

HCID 12658782Methyl 3-(benzyloxy)-5-methoxybenzoateYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 4.0 g (0.0165 mmol) methyl 3-(benzyloxy)-5-hydroxybenzoate (160), 6.84 g (0.0495 mmol) potassium carbonate, and 11.71 g (0.0825 mmol) iodomethane in the 200 mL of acetone was stirred at room temperature for 24 h. After the mixture was filtered and evaporated, the residue was washed with water. The methyl 3-(benzyloxy)-5-methoxybenzoate (161) was obtained as a white solid.

Workup

  1. filtrationAfter the mixture was filtered
  2. customevaporated
  3. washthe residue was washed with water

Sources & evidence

ORD record
ord-34cdac811085477c8b89e990af9512d2
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Reaction notes

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