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

HRID 31631

Reaktionsgleichung

Reaktionsgleichung von HRID 31631
[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].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>>[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 4

HCID 8285PentaerythritolHCID 8471TriethylamineHCID 66221Triethyl orthoacetateHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 13547990(1-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methanolAusbeute 48,2 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of pentaerythritol (15 g, 110 mmol), triethyl orthoacetate (20.2 ml, 110 mmol), and p-toluenesulfonic acid monohydrate (947 mg, 5.5 mmol) was stirred at 100° C. for 30 minutes. The temperature of the mixture was further raised to 130° C. and the mixture was stirred for 30 minutes. To the reaction mixture, triethylamine (1.53 ml, 11 mmol) was added and the reaction mixture was concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to obtain the title compound (8.5 g, yield: 48.2%) as a light yellow solid.

Aufarbeitung

  1. temperatureThe temperature of the mixture was further raised to 130° C.
  2. stirringthe mixture was stirred for 30 minutes
  3. concentrationthe reaction mixture was concentrated
  4. customThe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b4bd0363c7514f7294656ead7bf347c2
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

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