Allyl bromide → 2'-Allyloxyacetophenone

HRID 475552Notes

Reaction equation

HRID 475552 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[CH:18]=[CH2:19]>C(#N)C>[CH2:19]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9])[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 83752'-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 2994412'-Allyloxyacetophenone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 25 g quantity of 1-(2-hydroxyphenyl)ethanone and 76 g of potassium carbonate were suspended in 500 ml of acetonitrile, and 31 ml of allyl bromide was added. The mixture was stirred at room temperature for 48 hours. The reaction mixture was filtered to remove insolubles, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 34 g of pale yellow oily 1-(2-allyloxyphenyl)ethanone.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove insolubles
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-d2e934a9b5d34f48a77876e6507ba3b2
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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