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

HRID 562987

Reaction equation

HRID 562987 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+]>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

5

Reactant 3

HCID 2214AcetovanilloneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 992151-(4-Benzyloxy-3-methoxy-phenyl)-ethanoneYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxy-3-methoxyacetophenone (40 g, 240 mmol), benzyl bromide (31.4 mL, 260 mmol) and potassium carbonate (99.6 g, 360 mmol) in DMF (800 mL) was heated to 40° C. overnight. The solution was cooled to room temperature, poured over ice and the resultant solid was filtered. This material was washed with water and dried to give 1-(4-benzyloxy-3-methoxyphenyl)ethanone (61 g, 99%).

Workup

  1. additionpoured over ice
  2. filtrationthe resultant solid was filtered
  3. washThis material was washed with water
  4. customdried

Sources & evidence

ORD record
ord-7c89cf64e9c047d1bc5da2a27a906c90
Source dataset
uspto-grants-2011_11
Patent number
US08067436B2

Linked notes

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