Cyclohexene → 7-Decyl-2-methylnaphthalen-1-ol

Participants

Reaction Steps

To a mixture of 2-benzoyloxymethylene-7-n-decyl-1-tetralone (14 g, 33.5 mmoles) and Pd/C (3.5 g) under inert atmosphere was added cyclohexene (175 mL). The mixture was heated to reflux while maintaining the inert atmosphere. The conversion of starting material to product was determined by TLC after 3 hours. After all the starting material reacted, the mixture was cooled down to RT. The catalyst was removed by filtration and washed twice with 50 mL hot toluene. The combined filtrate was evaporated to a small volume. The product was purified with a Prep-500 silica gel column (a high pressure silica gel preparative column, obtained from Waters Association, Milford, MA). Toluene was used as the mobile phase. The product fractions were pooled and evaporated to dryness under vacuum overnight. Cream white solid (9.0 g; 90% yield) was recovered. The melting point was 65°-67° C.

Provenance & Evidence