Sodium Hydroxide → (3,6-Dimethyl-1,2-phenylene)dimethanol

Participants

Reaction Conditions

Reaction Steps

A 1 L 3-necked RBF is charged with a 1.0M lithium aluminium hydride solution in tetrahydrofuran (175 mL, 0.175 mol) and anhydrous tetrahydrofuran (100 mL) under nitrogen. The solution is cooled to −78° C. and a solution of 1,7-dimethyl-4,10-dioxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione 2 (12.3 g, 0.070 mol) in anhydrous tetrahydrofuran (150 mL) is added from a dropping funnel over a period of 30 minutes The reaction mixture is heated to reflux and stirred for 45 h. The reaction mixture is cooled to 0° C. using an ice bath and 2M sodium hydroxide solution (20 mL) is slowly added dropwise. The mixture is allowed to warm up to 22° C. and the precipitate is filtered off and washed thoroughly with diethyl ether and tetrahydrofuran. The filtrate is concentrated in vacuo.

Provenance & Evidence