Water → 1-(4-Benzyloxy-3-methoxy-phenyl)-ethanone

HRID 2277399Notes

Reaction equation

HRID 2277399 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1)=[O:3].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:13]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][C:6]=1[O:11][CH3:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2214AcetovanilloneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 992151-(4-Benzyloxy-3-methoxy-phenyl)-ethanoneYield 98.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-hydroxy-3-methoxyacetophenone (40 g, 240 mmol), benzyl bromide (34.1 mL, 260 mmol) and potassium carbonate (50.0 g, 360 mmol) in DMF (800 mL) was stirred at 40° C. for 5 hours. The reaction was cooled to room temperature and poured into a mixture of ice and water (2000 mL). The solid was collected by filtration, washed with water and dried in vacuo to give the title compound as a white solid (60.66 g, 98%).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-331c8280ab00499ea1a7904bc5961821
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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