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

HRID 36831

Reaction equation

HRID 36831 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]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:1][CH2:2][C:3]12[CH2:8][O:9][C:10]([CH3:11])([O:7][CH2:6]1)[O:5][CH2:4]2

Participants

5

Reactant 2

HCID 8285PentaerythritolHCID 66221Triethyl orthoacetate

Product 1

HCID 13547990(1-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methanolYield 93%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

To a suspension of pentaerythritol (13.6 g, 0.100 mol) in 10 mL of toluene was added freshly distilled triethyl orthoacetate (16.2 g. 18.3 mL, 0.100 mol) and p-toluenesulfonic acid monohydrate (50 mg). The mixture was slowly heated in an oil bath and ethanol was distilled from the mixture over a period of 12 hrs. After removal of the ethanol, the bath temperature was raised to 125° C. and toluene was distilled off until the solution was homogeneous (about 30 mL). The residue was sublimed (bulb to bulb, ~130--C, 2.5 mmHg) to give 4-(hydroxymethyl)-1-methyl-2,6,7-trioxabicyclo[2.2.21octane (15.0 g, 0.093 mol, 93%).

Workup

  1. temperatureThe mixture was slowly heated in an oil bath
  2. distillationethanol was distilled from the mixture over a period of 12 hrs
  3. customAfter removal of the ethanol
  4. distillationtoluene was distilled off until the solution

Sources & evidence

ORD record
ord-e5b0a5a437214e178861c3fb40b0c683
Source dataset
uspto-grants-1995_05
Patent number
US05417959

Linked notes

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