1-[2-(ALLYLOXY)-6-HYDROXYPHENYL]ETHAN-1-ONE synthesis

Yield:23226-84-8 305 gm (80%)

Reaction Conditions:

with potassium carbonate in acetone;

Steps:

25.a (a)

(a) Preparation of 2-hydroxy-6-allyloxyacetophenone A mixture of 2,6-dihydroxyacetophenone (300 gm; 1.97 moles), potassium carbonate (271 gm; 1.97 moles), and allyl bromide (271 mLs; 2.25 moles) in acetone (10 liters) was refluxed for a period of 3 hours. The reaction mixture was cooled, filtered through Celite and concentrated in vacuo. The residue was chromatographed on silica gel using toluene as eluent to yield 305 gm (80%) of 2-hydroxy-6-allyloxyacetophenone, mp. 54°-55° C. ¹ H NMR 2.40 (s, 3H, CH₃), 4.57 (d,J=6 Hz, 2H,OCH₂), 5.57 (m, 1H, CH), 6.33 (m, 2H, CH₂, 6.62 (d, J=9 Hz, 1H, proton ortho to hydroxyl), 6.83 (d,J=9 Hz, 1H, proton ortho to allyloxy), 7.72 (t, J=9 Hz, 1H, proton para to acetyl). Anal. Calcd for C₁₁ H₁₂ O₃: C, 68.75; H, 6.25. Found: C, 68.66; H, 6.54.

References:

US4863958,1989,A