Benzyl Bromide → Methyl 4-(benzyloxy)-2-hydroxybenzoate

HRID 508185Notes

Reaction equation

HRID 508185 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1>CC(C)=O>[CH2:25]([O:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([OH:1])[CH:11]=1)[C:22]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 225489Methyl 4-(benzyloxy)-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 2,4-dihydroxybenzoate (i-1a) (1.68 g, 10 mmol) in acetone (30 mL) was added K2CO3 (2.76 g, 20 mmol). The mixture was stirred at rt for 5 h, followed by the addition of BnBr (1.88 g, 11 mmol). The mixture was heated at 60° C. for 24 h. The reaction mixture was cooled down, filtered. The filtrate was concentrated to afford the title compound. LCMS (ESI) calc'd for C15H14O4 [M+H]+: 259.1. found: 259.1.

Workup

  1. temperatureThe mixture was heated at 60° C. for 24 h
  2. temperatureThe reaction mixture was cooled down
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8291ca4c218d461987893b0a52eb7a02
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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