Benzyl Bromide → Methyl 3-(benzyloxy)benzoate

HRID 610415Notes

Reaction equation

HRID 610415 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH2:14]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 13368031Methyl 3-(benzyloxy)benzoateYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (0.395 g, 9.87 mmol, 60% in mineral oil) in DMF (20 mL) was added methyl 3-hydroxybenzoate (1.0 g, 6.58 mmol). After stirring for 15 min at room temperature, benzyl bromide (1.1 g, 6.58 mmol) was added. After stirring at room temperature for 3 h, the solution was partitioned between ethyl acetate and water. The organic layer was washed with water (2×75 mL), saturated aqueous sodium bicarbonate, and brine, then dried (MgSO4), filtered and concentrated to yield an off-white solid (1.013 g, 4.2 mmol). 1H NMR (400 MHz, CDCl3)δ 7.67 (m, 2H), 7.48-7.34 (m, 6H), 7.19 (m, 1H), 5.12 (s, 2H), 3.95 (s, 3H).

Workup

  1. stirringAfter stirring at room temperature for 3 h
  2. customthe solution was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water (2×75 mL), saturated aqueous sodium bicarbonate, and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fe4dcdcd2beb4bbca779def56168065e
Source dataset
uspto-grants-1999_12
Patent number
US05998470

Reaction notes

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