Benzyl Bromide → Methyl 3-(benzyloxy)-5-isopropoxybenzoate

HRID 1990132Notes

Reaction equation

HRID 1990132 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH3:14][CH:13]([O:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([O:1][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:15]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 23072925Methyl 3-hydroxy-5-isopropoxybenzoate

Product 1

HCID 59127144Methyl 3-(benzyloxy)-5-isopropoxybenzoateYield 103.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-hydroxy-5-[(1-methylethyl)oxy]benzoate (25 g) in DMF (250 mL) was added anhydrous potassium carbonate (297 mmol), and benzyl bromide (143 mmol). The mixture was stirred at 60° C. for 5 hours, then cooled to room temperature. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The organics were combined and washed with further water, brine, dried (MgSO4) and concentrated in vacuo to give the desired compound (37 g) which was used without further purification.

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. washwashed with further water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9b3427f00384b6cbb5a7db9835aa88d
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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