Hexane → HCID 19907485, compound

Participants

Reaction Steps

To 17.5 ml of absolute n-hexane were added 530 mg of o-xylene and 1.40 g of potassium tert.-butoxide, followed by dropwise addition of 8.4 ml of 1.6M n-butyl lithium in n-hexane over 5 minutes with stirring at a room temperature, and the mixture was refluxed for an hour to obtain a vermilion-colored suspension. The suspension was cooled with dry ice/acetone, and after adding at once solution of 4.46 g 2-(3-bromopropyloxy)tetrahydropyran in 2.5 ml of absolute n-hexane with stirring, further stirred for 5 minutes, warmed to a room temperature, and stirred overnight. To a yellow suspension thus obtained were added 20 ml of ice water and 50 ml of n-hexane. The organic layer was separated, washed with water and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated under a reduced pressure. The resulting oily residue was applied to a silica gel column, and eluted with hexane/ethyl acetate (20:1) to obtain 747 mg of crude 1,2-bis[4-(2-tetrahydropyranyloxy)butyl]benzene as a colorless liquid.

Provenance & Evidence