Sodium Chloride → Benzyl 4-(benzyloxy)-3-methoxybenzoate

HRID 993190Notes

Reaction equation

HRID 993190 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[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.[Cl-].[Na+]>CN(C)C=O.O>[CH2:19]([O:11][C:1](=[O:12])[C:2]1[CH:10]=[CH:9][C:7]([O:8][CH2:1][C:2]2[CH:10]=[CH:9][CH:7]=[CH:4][CH:3]=2)=[C:4]([O:5][CH3:6])[CH:3]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7498Benzyl BromideHCID 8468Vanillic AcidHCID 11430Potassium Carbonate

Product 1

HCID 22070405Benzyl 4-(benzyloxy)-3-methoxybenzoateYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 52.6 g (313 mmol) of commercially available vanillic acid in 250 ml of dimethylformamide was slowly added 129.8 g (939 mmol) of potassium carbonate under ice-cooling, and78.2ml (657 mmol) of benzylbromide was slowly added thereto, followed by overnight stirring in an atmosphere of argon at room temperature. The reaction mixture was poured into water, and sodium chloride was added thereto. The precipitated crystals were collected by filtration, washed with water, and dried to give 104.2 g (96%) of 4-benzyloxy-3-methoxybenzoic acid benzyl ester.

Workup

  1. temperaturecooling
  2. additionwas added
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-4564cccff8434074801cc4ea59642d1c
Source dataset
uspto-grants-2002_10
Patent number
US06472391B2

Reaction notes

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