1,2,3,4-Tetrahydro-2-naphthoic acid → (1,2,3,4-Tetrahydronaphthalen-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of 1,2,3,4-tetrahydro-2-naphthoic acid (2.50 g, 14.2 mmol) in 100 ml THF was treated with LiAlH4 (681 mg, 17.04 mmol) and the reaction mixture was heated at reflux for 5 hours. The suspension was cooled to 0° C. and quenched by addition of solid Na2SO4▪10H2O. The mixture was stirred at room temperature for 4 hours. The solid was removed by filtration. Concentration of filtrate in vacuo gave a yellowish oil (2.28 g, 98.8%); 1H NMR (CDCl3, 300 MHz) δ1.43 (m, 1H), 2.00 (m, 2H) 2.51 (dd, J1=16.5 Hz, J2=10.8 Hz, 1H), 2.85 (m, 3H), 3.65 (dd, J1=6.3 Hz, J2=1.2 Hz, 2H), 7.09 (s, 4H).

Provenance & Evidence