Water → Benzyl 4-benzoyloxy-2-benzyloxybenzoate

HRID 2220600Notes

Reaction equation

HRID 2220600 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:17][C:18]1[CH:33]=[CH:32][C:21]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])=[C:20]([OH:34])[CH:19]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[C:9]([O:17][C:18]1[CH:33]=[CH:32][C:21]([C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23])=[C:20]([O:34][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:19]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 23134101Benzyl 4-benzoyloxy-2-hydroxybenzoate

Product 1

HCID 23090801Benzyl 4-benzoyloxy-2-benzyloxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (0.80 mL) was added to a mixture of benzyl 4-benzoyloxy-2-hydroxybenzoate (2.23 g) and cesium carbonate (2.29 g) in N,N-dimethylformamide (10 mL) at room temperature with stirring, and the mixture was stirred at 50° C. for 3 hrs. Water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=6/1) to afford benzyl 4-benzoyloxy-2-benzyloxybenzoate (2.87 g).

Workup

  1. stirringthe mixture was stirred at 50° C. for 3 hrs
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-236a8b25aeea442bb63ca33203f5bd4c
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

Loading…