Sulfuric Acid → 1-Octyn-3-ol, 3,6-dimethyl-

HRID 68011

Reaktionsgleichung

Reaktionsgleichung von HRID 68011
[CH3:1][CH:2]([CH2:8][CH3:9])[CH2:3][CH2:4][C:5](=[O:7])[CH3:6].[C:10]([Mg]Cl)#[CH:11].S(=O)(=O)(O)O>O1CCCC1>[CH3:6][C:5]([OH:7])([CH2:4][CH2:3][CH:2]([CH3:1])[CH2:8][CH3:9])[C:10]#[CH:11]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 289655-Methyl-2-heptanoneHCID 178462451HCID 178462451, Verbindung

Produkt 1

HCID 1742441-Octyn-3-ol, 3,6-dimethyl-Ausbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

128 g (1 mole) of 5-methyl-heptan-2-one are added in the course of 1 hour, with stirring, to 1 liter of a 1.1 molar solution of ethynyl-magnesium chloride in tetrahydrofuran at 10° C. After allowing about a further hour's reaction, the mixture is worked up. To do so, 2 N sulfuric acid is added, whilst cooling with ice, until two clear phases are present. The organic phase is then separated off and washed neutral with water, if necessary, and the tetrahydrofuran is distilled off at 50° C./67 mbar. The residue is subjected to fractional distillation. 143 g of main fraction, boiling at 50°-52° C./0.01 mbar, are obtained; nD25 =1.4411. This corresponds to a yield of 93%. Scent: predominantly floral, woody, herbal, minty with a spicy, slightly animal after-scent.

Aufarbeitung

  1. customAfter allowing about a further hour's reaction
  2. temperaturewhilst cooling with ice, until two clear phases
  3. customThe organic phase is then separated off
  4. washwashed neutral with water
  5. distillationif necessary, and the tetrahydrofuran is distilled off at 50° C./67 mbar
  6. distillationThe residue is subjected to fractional distillation
  7. custom143 g of main fraction, boiling at 50°-52° C./0.01 mbar, are obtained

Quellen und Nachweise

ORD-Eintrag
ord-ec909e227fbe440faa5cc39a5bd828a5
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04347388

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