Toluene → 2-Pentyl-4,4,7,7-tetramethyl-4,7-dihydro-1,3-dioxepin

HRID 34430

Reaktionsgleichung

Reaktionsgleichung von HRID 34430
[CH3:1][C:2]([OH:10])([CH:4]=[CH:5][C:6]([CH3:9])([OH:8])[CH3:7])[CH3:3].[CH:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH2:12]([CH:11]1[O:10][C:2]([CH3:3])([CH3:1])[CH:4]=[CH:5][C:6]([CH3:9])([CH3:7])[O:8]1)[CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 6184HexanalHCID 3499742,5-Dimethyl-3-hexene-2,5-diol

Produkt 1

HCID 212847002-Pentyl-4,4,7,7-tetramethyl-4,7-dihydro-1,3-dioxepinAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 720 g (5 moles) of 2,5-dimethylhex-3-ene-2,5-diol, 3 g of p-toluenesulfonic acid, 500 g (5 moles) of n-hexanal and 1 l of toluene was refluxed, and the resulting water of reaction (115 ml) was separated off in the course of 5.5 h. The mixture was then left to cool, 10 ml of a 25% strength aqueous sodium hydroxide solution were added, the mixture was washed neutral with a little water and the toluene was removed under reduced pressure at from 50° to 60° C. The residue obtained was distilled under 0.1 mbar to give 796 g of 2-pentyl-4,4,7,7-tetramethyl-4,7-dihydro-1,3-dioxepin of boiling point 75° C./0.1 mbar.

Aufarbeitung

  1. temperaturewas refluxed
  2. customwas separated off in the course of 5.5 h
  3. waitThe mixture was then left
  4. temperatureto cool
  5. addition10 ml of a 25% strength aqueous sodium hydroxide solution were added
  6. washthe mixture was washed neutral with a little water
  7. customthe toluene was removed under reduced pressure at from 50° to 60° C
  8. customThe residue obtained
  9. distillationwas distilled under 0.1 mbar

Quellen und Nachweise

ORD-Eintrag
ord-204a7f32307348a1bc31f43769c92109
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761489

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