Benzyl Chloride → 1-(4-(Benzyloxy)phenyl)-2-(4-methoxyphenyl)ethanone

HRID 1425792Notes

Reaction equation

HRID 1425792 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C>[CH2:25]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:18])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:6][CH:7]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 126053601-(4-Hydroxyphenyl)-2-(4-methoxyphenyl)ethanone

Product 1

HCID 189237831-(4-(Benzyloxy)phenyl)-2-(4-methoxyphenyl)ethanoneYield 30.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 0° C. solution of 1-(4-hydroxyphenyl)-2-(4-methoxyphenyl)ethanone (3.0 g, 0.01 mol) in acetonitrile (60 mL) under an inert atmosphere was added potassium carbonate (3.4 g, 0.02 mol) followed by benzyl chloride (1.8 mL, 0.014 mol). The reaction mixture was brought to 80° C. and stirred for 2 h. The reaction was quenched with cold water, filtered and the filtrate was extracted with DCM (2×100 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford 1-(4-(benzyloxy)phenyl)-2-(4-methoxyphenyl)ethanone (1.0 g, 24%) as a white solid.

Workup

  1. customwas brought to 80° C.
  2. customThe reaction was quenched with cold water
  3. filtrationfiltered
  4. extractionthe filtrate was extracted with DCM (2×100 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b628c4f737741b19c8efae7d1d90675
Source dataset
uspto-grants-2015_01
Patent number
US08933074B2

Reaction notes

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