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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence