Water → Ethyl 4-(benzyloxy)-2-(methoxymethoxy)-6-methylbenzoate

HRID 1888730Notes

Reaction equation

HRID 1888730 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[C:18]([CH3:20])[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([OH:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][O:29][CH2:30]Br.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:19]=[C:18]([CH3:20])[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([O:21][CH2:28][O:29][CH3:30])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 83093Bromomethyl methyl etherHCID 14408138Ethyl 4-(benzyloxy)-2-hydroxy-6-methylbenzoate

Product 1

HCID 59467099Ethyl 4-(benzyloxy)-2-(methoxymethoxy)-6-methylbenzoateYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-(benzyloxy)-2-hydroxy-6-methylbenzoate (15.0 g, 52.4 mmol) in DMF (100 mL) were added potassium carbonate (14.5 g, 105 mmol) and bromomethyl methyl ether (6.40 mL, 78.5 mmol), and the mixture was stirred at room temperature for 20 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed twice with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 4:1) to give the title compound (14.9 g, yield 86%) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed twice with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 4:1)

Sources & evidence

ORD record
ord-d458a0d3a1114070b662b439a092612a
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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