Benzyl Bromide → 3-Benzyloxy-4-methylbenzoic acid benzyl ester

HRID 1674570Notes

Reaction equation

HRID 1674570 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1C)[C:5](O)=O.[C:12](=[O:15])([O-])[O-:13].[Cs+].[Cs+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:26](=[O:29])(O)[O-].[Na+]>CN(C)C=O>[CH2:18]([O:13][C:12](=[O:15])[C:10]1[CH:2]=[CH:3][C:4]([CH3:5])=[C:8]([O:29][CH2:26][C:2]2[CH:3]=[CH:4][CH:8]=[CH:9][CH:10]=2)[CH:9]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 685123-Hydroxy-4-methylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 584372413-Benzyloxy-4-methylbenzoic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxy-4-methylbenzoic acid (5.0 g) in N,N-dimethylformamide (100 mL) were added cesium carbonate (32 g) and benzyl bromide (12 g) at the same temperature and this mixture was stirred at room temperature for 2 days. To this reaction mixture was added a saturated aqueous sodium bicarbonate solution and this mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and this residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (7.5 g).

Workup

  1. extractionthis mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthis residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a2842f05d6fa4024a5c2da87d14e8127
Source dataset
uspto-grants-2011_08
Patent number
US08003647B2

Reaction notes

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