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

HRID 334878Notes

Reaction equation

HRID 334878 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-fb055f8b97524905850963d1066ad371
Source dataset
uspto-grants-2014_11
Patent number
US08883790B2

Reaction notes

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