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

HRID 280424

Reaktionsgleichung

Reaktionsgleichung von HRID 280424
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-172a36ec004d4280a9e8dd6b6ac19b11
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04588849

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