Benzyl Bromide → Benzyl 3-(benzyloxy)-4-methoxybenzoate

HRID 61639Notes

Reaction equation

HRID 61639 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:6]([O:7][CH3:8])=[C:4]([OH:5])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.[Cl-].[Na+].O>[CH2:19]([O:5][C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][C:6]=1[O:7][CH3:8])[C:1]([O:12][CH2:1][C:2]1[CH:10]=[CH:9][CH:6]=[CH:4][CH:3]=1)=[O:11])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7498Benzyl Bromide2×HCID 11430Potassium CarbonateHCID 12575Isovanillic Acid

Product 1

HCID 22070447Benzyl 3-(benzyloxy)-4-methoxybenzoateYield 180.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To an ice cold mixture of isovanillic acid 1 (4.3 g, 25.5 mmol) and K2CO3 (10.5 g, 0.152 mol) in anhydrous DMF (40 mL) was added benzyl bromide (8.7 g, 6.05 mL, 51.1 mmol). The resulting reaction mixture stirred at RT overnight. An additional aliquot of benzyl bromide was added (1.0 ml) and stirring was continued for 1.5 h. The reaction mixture was poured into brine (100 mL) and the solid was collected via filtration, washed with water and dried under high vacuum to give benzyl 3-(benzyloxy)-4-methoxybenzoate as a white solid (7.99 g, 23.0 mmol, 90%).

Workup

  1. customThe resulting reaction mixture
  2. stirringstirring
  3. waitwas continued for 1.5 h
  4. filtrationthe solid was collected via filtration
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-b8bb8dcd3c004e2d9534c17f0e7b911b
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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