Benzyl Bromide → Methyl 5-acetyl-2,4-bis-benzyloxybenzoate

HRID 425141Notes

Reaction equation

HRID 425141 reaction equation
[C:1]([C:4]1[C:5]([OH:15])=[CH:6][C:7]([OH:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C>[C:1]([C:4]1[C:5]([O:15][CH2:1][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:13]=2)=[CH:6][C:7]([O:14][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 12482079Methyl 5-acetyl-2,4-dihydroxybenzoate

Product 1

HCID 11955869Methyl 5-acetyl-2,4-bis-benzyloxybenzoateYield 142.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 5-acetyl-2,4-dihydroxybenzoate (2.62 g, 12.48 mmol) was dissolved in acetonitrile (40 ml), anhydrous potassium carbonate (4.93 g, 35.7 mmol) was added and the stirred mixture was treated with benzyl bromide (5.09 g, 29.75 mmol) and held at reflux for 3 hours. Upon cooling the solvent was removed in vacuo and the mixture partitioned between water and dichloromethane. The organic layer was separated and the solvent removed in vacuo to afford methyl 5-acetyl-2,4-bis-benzyloxybenzoate (3.48 g, 71%) as a colourless solid which was dried at 50° C. in a vacuum oven and used without further purification. 1H NMR (DMSO-d6) 8.21 (1H, s), 7.55 (4H, m), 7.43 (4H, m), 7.37 (2H, m), 7.04 (1H, s), 5.38 (4H, s), 3.79 (3H, s), 2.48 (3H, s). MS: [M+H]+ 391.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureUpon cooling the solvent
  3. customwas removed in vacuo
  4. customthe mixture partitioned between water and dichloromethane
  5. customThe organic layer was separated
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0fa9c795cee6453eb4b1be720feb42e3
Source dataset
uspto-grants-2012_01
Patent number
US08106057B2

Reaction notes

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