Propylethinylcarbinol → 1-(3-Hydroxyhex-1-yn-1-yl)-2,2,6-trimethylcyclohexan-1-ol

Reaction equation

[OH-].[K+].[CH3:3][CH:4]1[CH2:9][CH2:8][CH2:7][C:6]([CH3:11])([CH3:10])[C:5]1=[O:12].[CH:13]#[C:14][CH:15]([OH:19])[CH2:16][CH2:17][CH3:18]>C(OCC)C>[OH:12][C:5]1([C:13]#[C:14][CH:15]([OH:19])[CH2:16][CH2:17][CH3:18])[C:6]([CH3:11])([CH3:10])[CH2:7][CH2:8][CH2:9][CH:4]1[CH3:3]

Participants

Procedure

In a three-necked vessel of 250 ml equipped with a thermometer, a condenser and a dropping funnel, there were placed 23.9 g (0.427M) of finely ground KOH and 50 ml of anhydrous diethyl ether. 14 G (0.1M) of 2,6,6-trimethylcyclohexanone and 13.5 g (0.138M) of hex-1-yn-3-ol were then added dropwise to the obtained suspension. The addition is slightly exothermic. After standing for 24 h, the mixture was poured onto ice and extracted with ether while the combined extracts were washed with a 10% HCl solution, with brine until neutrality and finally dried over Na2SO4 and concentrated. A fractional distillation of the obtained residue gave 12 g of 1-(1-hydroxy-2,6,6-trimethylcyclohexyl)-hex-1-yn-3-ol having b.p. 100°-125°/13.3 Pa.