Dichloromethane → 3-(4-Benzyloxy-3-methoxy-phenyl)-propionic acid benzyl ester

HRID 458786

Reaction equation

HRID 458786 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[O:13][CH3:14].C([O-])([O-])=O.[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(Cl)Cl>CC(C)=O>[CH2:21]([O:11][C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:8][C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)=[C:3]([O:13][CH3:14])[CH:4]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14340Dihydroferulic Acid

Product 1

HCID 693534603-(4-Benzyloxy-3-methoxy-phenyl)-propionic acid benzyl esterYield 180.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-(4-hydroxy-3-methoxy-phenyl)-propionic acid (5.1 g, 25.99 mmol), anhydrous K2CO3 (25 g, 180.88 mmol) and benzyl bromide (7.5 ml, 63.14 mmol) in anhydrous acetone (100 ml) was stirred at reflux for 7.5 h under nitrogen. After cooling, the reaction mixture was filtered and concentrated in vacuo. Flash chromatography (CH2Cl2) gave the title compound (8.83 g, 23.45 mmol, 90%).

Workup

  1. temperatureat reflux for 7.5 h under nitrogen
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7466c945d5f9454a84cc85d0aed68e9a
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Linked notes

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