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

HRID 334981Notes

Reaction equation

HRID 334981 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][C:17](=[O:29])[C:18]1[CH:23]=[C:22]([C:24](=[O:26])[CH3:25])[C:21]([OH:27])=[CH:20][C:19]=1[OH:28]>C(#N)C>[C:24]([C:22]1[C:21]([O:27][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:20][C:19]([O:28][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:18]([CH:23]=1)[C:17]([O:16][CH3:15])=[O:29])(=[O:26])[CH3:25]

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 97.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of benzyl bromide (16.14 L, 136 mol) and anhydrous potassium carbonate (20.25 Kg, 147.6 mol) in acetonitrile (184.5 L) was added methyl 5-acetyl-2,4-dihydroxybenzoate (14 Kg, 66.6 mol, step 2) in 6 portions over 5 h. The mixture was stirred and held at reflux for 20 hours, cooled to room temperature the mixture was poured onto water (682 L) and stirred vigorously for 2 hours. The solids were collected by centrifugation and dried under reduced pressure to constant mass in a vacuum oven at 60° C. overnight to afford methyl 5-acetyl-2,4-bis-benzyloxybenzoate (23.5 Kg, 97.3%) as a cream solid mp 114-115° C.

Workup

  1. temperatureat reflux for 20 hours
  2. additionwas poured onto water (682 L)
  3. stirringstirred vigorously for 2 hours
  4. customThe solids were collected by centrifugation
  5. customdried under reduced pressure to constant mass in a vacuum oven at 60° C. overnight

Sources & evidence

ORD record
ord-c60e11b2c50a4f1cb9d49a1687f62962
Source dataset
uspto-grants-2014_11
Patent number
US08883790B2

Reaction notes

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