Pentaerythritol → (1-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methanol

HRID 2260793

Reaktionsgleichung

Reaktionsgleichung von HRID 2260793
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[C:10](OCC)(OCC)(OCC)[CH3:11].C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>C(OCCCCCCCC)(=O)C1C(=CC=CC=1)C(OCCCCCCCC)=O>[CH3:10][C:11]12[O:7][CH2:6][C:3]([CH2:8][OH:9])([CH2:4][O:5]1)[CH2:2][O:1]2

Komponenten

5

Edukt 3

HCID 8285PentaerythritolHCID 66221Triethyl orthoacetateHCID 161440Pyridine 4-methylbenzene-1-sulfonate

Produkt 1

HCID 13547990(1-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methanolAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8346di-N-Octyl PhthalateLösungsmittel

Versuchsvorschrift

Pentaerythritol (13.6 g, 0.1 mol), triethyl orthoacetate (16.22 g, 0.1 mol, 18.3 mL), pyridine p-toluenesulfonate (PPTS) (0.5 g, 2 mmol) and 100 mL of dioctyl phthalate were mixed in a 250 mL, round-bottom flask fitted with a regular distillation apparatus. The mixture was heated to 130°-140° C. and ethanol was slowly distilled. When the amount of ethanol was close to the theoretical value the pressure was reduced to <0.1 torr and the product was distilled in vacuo. The white product which distilled crystallized in the condenser to give 13.6-14.9 g of MHTBO. Yield: 85-93%. The compound can be recrystallized from toluene but can be used directly. Mp: 110°-112° C.

Aufarbeitung

  1. customfitted with a regular distillation apparatus
  2. temperatureThe mixture was heated to 130°-140° C.
  3. distillationethanol was slowly distilled
  4. customWhen the amount of ethanol was close to the theoretical value the pressure
  5. distillationthe product was distilled in vacuo
  6. distillationThe white product which distilled
  7. customcrystallized in the condenser
  8. customto give 13.6-14.9 g of MHTBO
  9. customThe compound can be recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-888103a365844a97931382d5cab0ce23
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05478924

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