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

HRID 280424

Reaction equation

HRID 280424 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

5

Reactant 3

HCID 7746PropylethinylcarbinolHCID 14797Potassium HydroxideHCID 170002,2,6-Trimethylcyclohexanone

Product 1

HCID 202260351-(3-Hydroxyhex-1-yn-1-yl)-2,2,6-trimethylcyclohexan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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.

Workup

  1. customIn a three-necked vessel of 250 ml equipped with a thermometer, a condenser and a dropping funnel, there
  2. additionThe addition
  3. additionthe mixture was poured onto ice
  4. extractionextracted with ether while the combined extracts
  5. washwere washed with a 10% HCl solution, with brine until neutrality
  6. dry with materialfinally dried over Na2SO4
  7. concentrationconcentrated
  8. distillationA fractional distillation of the obtained residue

Sources & evidence

ORD record
ord-172a36ec004d4280a9e8dd6b6ac19b11
Source dataset
uspto-grants-1986_05
Patent number
US04588849

Linked notes

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