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

HRID 643945Notes

Reaction equation

HRID 643945 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11].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>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:6][C:5]=1[OH:11]

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 (10 g, 59.5 mmol) in acetone (200 mL) at 0° C. is added K2CO3 (30 g, 217 mmol), followed by benzyl bromide (7.72 mL, 65 mmol). The solution is warmed to ambient temperature and stirred for 48 h. The mixture is filtered and the solvent removed under reduced pressure. The crude oil is dissolved in EtOAc and washed with water, saturated NaHCO3, and dried over sodium sulfate. The solvent is removed under reduced pressure and the solid purified by flash chromatography using hexane/EtOAc (10:1) to afford 4-benzyloxy-2-hydroxybenzoic acid methyl ester as a white powder: 1H NMR (CDCl3) δ 10.93 (s, 1H), 7.73 (d, J=9.09 Hz, 1H), 7.42-7.33 (m, 5H), 6.53-6.49 (m, 2H), 5.07 (s, 2H), 3.90 (s, 3H); (M+H)+=259.

Workup

  1. filtrationThe mixture is filtered
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe crude oil is dissolved in EtOAc
  4. washwashed with water, saturated NaHCO3
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is removed under reduced pressure
  7. customthe solid purified by flash chromatography

Sources & evidence

ORD record
ord-09f49ac13b4f4b43a711ff35db314761
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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