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

HRID 334976Notes

Reaction equation

HRID 334976 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([C:12]1[C:13]([OH:23])=[CH:14][C:15]([OH:22])=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18])(=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:9]([C:12]1[C:13]([O:23][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][C:15]([O:22][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18])(=[O:11])[CH3:10]

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 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl bromide (70 ml, 0.59 mol) was added to a stirred mixture of methyl 5-acetyl-2,4-dihydroxybenzoate (60.7 g, 0.29 mol) and anhydrous potassium carbonate (87.8 g, 0.64 mol) in acetonitrile (800 ml) and the mixture was stirred and held at reflux for 16 hours. Upon cooling to room temperature the mixture was poured onto water (3 L) and stirred vigorously for 2 hours. The solids were collected by filtration, rinsed with water (2 L), sucked dry under reduced pressure and dried to constant mass in a vacuum oven at 60° C. overnight to afford methyl 5-acetyl-2,4-bis-benzyloxybenzoate (112.1 g, 99%) as a cream solid. 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 16 hours
  2. additionwas poured onto water (3 L)
  3. stirringstirred vigorously for 2 hours
  4. filtrationThe solids were collected by filtration
  5. washrinsed with water (2 L)
  6. customsucked dry under reduced pressure
  7. customdried to constant mass in a vacuum oven at 60° C. overnight

Sources & evidence

ORD record
ord-cc661aefd8db473b8bd90d6a34a79033
Source dataset
uspto-grants-2014_11
Patent number
US08883790B2

Reaction notes

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