Allyl bromide → 1-(3-Allyl-2-hydroxyphenyl)ethanone

HRID 2255198Notes

Reaction equation

HRID 2255198 reaction equation
[OH-:1].[K+].O[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[CH2:13](Br)[CH:14]=[CH2:15]>CC(C)=O.CCCCCC>[CH2:13]([C:11]1[C:12]([OH:1])=[C:7]([C:5](=[O:6])[CH3:4])[CH:8]=[CH:9][CH:10]=1)[CH:14]=[CH2:15]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 130269161-(3-Allyl-2-hydroxyphenyl)ethanoneYield 77.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8058HexaneSolvent

Conditions

Temperature
165 °C

Procedure

A suspension of 6.2 g of potassium hydroxide, 10 g of 2-hydroxyacetophenone and 17.8 g of allyl bromide in 550 ml of acetone was refluxed for 16 hours, cooled and filtered. The solids were extracted with three 250 ml portions of chloroform and the combined acetone filtrate and chloroform extracts concentrated to give a residue which was then heated at 165° C. for 18 hours, cooled, diluted with 250 ml of hexane and filtered. The resulting filtrate was concentrated in vacuo to give 10.02 g of 3'-allyl-2'-hydroxyacetophenone as a liquid: TLC Rf 0.70 in 3:1 toluene-methyl isobutylketone; C-13 NMR (CDCl3): δ26.72, 33.41, 116.0, 118.44, 119.21, 128.82, 129.34, 136.10, 136.44, 160.40, 204.75; 1H-NMR (CDCl3): δ2.60 (s, 3H), 3.40 (d, J=6.4 Hz, 2H); 5.05 (d, J=1.4 Hz, 1H), 5.08-5.11 (m, 1H), 5.92-6.06 (m, 1H), 6.82 (t, J=7.6 Hz, 1H), 7.33 (d, J=6.7 Hz, 1H), 7.59 (d, J=6.7 Hz, 1H), 12.62 (s, 1H).

Workup

  1. temperaturewas refluxed for 16 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. extractionThe solids were extracted with three 250 ml portions of chloroform
  5. concentrationthe combined acetone filtrate and chloroform extracts concentrated
  6. customto give a residue which
  7. temperaturecooled
  8. filtrationfiltered
  9. concentrationThe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d9e2ff8442b84458841ee2d76a6b007f
Source dataset
uspto-grants-1993_08
Patent number
US05238954

Reaction notes

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