trans-4-Methyl-1-p-tolyl-1-penten-3-ol → 2-Methyl-5-(p-tolyl)-3-pentanol

Participants

Reaction Steps

To a solution of trans-4-methyl-1-p-tolyl-1-penten-3-ol (43.2 g, 0.227 mol) in methanol (35 mL) was added 2 micro-spoon of palladium, 10% on activated carbon and the reaction mixture was hydrogenated overnight at 40 psi. The solution was diluted with ethyl acetate, filtered over celite and evaporated to give 40 g of 2-methyl-5-(p-tolyl)-3-pentanol as a colorless oil and used without further purification in the next step (step g). 1H NMR (300 MHz; CDCl3): 0.90 (d, J=6.9 Hz, 6 H), 1.70 (m, 4 H), 2.31 (s, 3 H), 2.62 (m, 1 H), 2.78 (m, 1 H), 3.39 (m, 1 H), 7.09 (s, 4 H).

Provenance & Evidence