Tetrahydrothiophene → 2-Phenyl-1-oxaspiro[2.5]octane

HRID 889682

Reaktionsgleichung

Reaktionsgleichung von HRID 889682
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S1CCCC1.[Cl-].C([S+]1CCCC1)C1C=CC=CC=1.[OH-].[K+].[C:29]1(=[O:35])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>CO.O>[C:2]1([CH:1]2[C:29]3([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[O:35]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 1127TetrahydrothiopheneHCID 7503Benzyl ChlorideHCID 7967CyclohexanoneHCID 14797Potassium Hydroxide2×HCID 86626231S-benzyltetrahydrothiophenium chloride

Produkt 1

HCID 2548142-Phenyl-1-oxaspiro[2.5]octaneAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture of 152 g (1.18 mol) of benzyl chloride, 108 g (1.18 mol) of tetrahydrothiophene and 0.225 L of water is stirred well at 85° C. until a homogeneous clear or slightly turbid single-phase solution of S-benzyltetrahydrothiophenium chloride has been obtained. The solution is cooled to 20° C. and is slowly added dropwise to a reaction mixture consisting of potassium hydroxide solution (prepared from 267 g (4.75 mol) of potassium hydroxide in 0.53 L of ice-water) and 467 g of cyclohexanone (4.75 mol) in 225 g of methanol. After the addition is complete, the reaction mixture is allowed to stand for 10 minutes until the phases have separated; the organic phase is separated off and subjected to fractional distillation. 181 g (80%) of 2-phenyl-1-oxa-spiro[2.5]octane are obtained in the form of a clear colourless oil.

Aufarbeitung

  1. customhas been obtained
  2. additionis slowly added dropwise to a reaction mixture
  3. additionAfter the addition
  4. customhave separated
  5. customthe organic phase is separated off
  6. distillationsubjected to fractional distillation

Quellen und Nachweise

ORD-Eintrag
ord-a08d88969042452693127dbad0239381
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252959B2

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