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

HRID 31631

Reaction equation

HRID 31631 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

HCID 13547990(1-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methanolYield 48.2%

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b4bd0363c7514f7294656ead7bf347c2
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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