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

HRID 38654

Reaction equation

HRID 38654 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoateYield 34%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 8.40 g (0.05 mmol) methyl 3,5-dihydroxybenzoate (159) and 7.60 g (0.055 mmol) of potassium carbonate in 250 mL of acetone was stirred at room temperature for 30 min. Then 8.55 g (0.05 mmol) of benzyl bromide dissolved in 100 mL of acetone was added. The suspension was refluxed for 24 h. The solid was filtered, and the filtrate was evaporated. The residue was purified by column chromatography (SiO2, CH2Cl2/EtOAc=9/1) to give 160.

Workup

  1. additionwas added
  2. temperatureThe suspension was refluxed for 24 h
  3. filtrationThe solid was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography (SiO2, CH2Cl2/EtOAc=9/1)

Sources & evidence

ORD record
ord-84eaaa2eaa734cbb920c9edc10073735
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Linked notes

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