Water → Methyl 5-(benzyloxy)-2-methoxybenzoate

HRID 1496981Notes

Reaction equation

HRID 1496981 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:19])=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:19][CH3:20])=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13026913Methyl 5-(benzyloxy)-2-hydroxybenzoate

Product 1

HCID 66775910Methyl 5-(benzyloxy)-2-methoxybenzoateYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 5-(benzyloxy)-2-hydroxybenzoate (10.6 g, 41.1 mmol) and K2CO3 (11.3 g, 82.2 mmol) in DMF (100 mL) was added iodomethane (2.60 mL, 49.3 mmol) drop wise over 5 minutes. The resulting mixture was stirred at room temperature overnight. The reaction mixture was poured into water (400 mL), filtered, and collected the solid. The solid was dissolved in EtOAc (300 mL), washed with water (50 mL) and brine (100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give methyl 5-(benzyloxy)-2-methoxybenzoate (10.4 g, 98%) as a yellow solid.

Workup

  1. filtrationfiltered
  2. customcollected the solid
  3. dissolutionThe solid was dissolved in EtOAc (300 mL)
  4. washwashed with water (50 mL) and brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-16cdeed421984f2d94e23f2dff802fd4
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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