Methanol → (4-Methoxyoxan-4-yl)methanol

HRID 1623246Notes

Reaction equation

HRID 1623246 reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH2:2]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[CH3:24][OH:25]>>[CH3:24][O:25][C:3]1([CH2:2][OH:1])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

4

Reactant 3

HCID 887MethanolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 1604391,6-Dioxaspiro[2.5]octane

Product 1

HCID 66937097(4-Methoxyoxan-4-yl)methanol

Conditions

Temperature
0 °C

Procedure

To a solution of 1,6-dioxaspiro[2.5]octane (600 mg, 5.26 mmol) in methanol (10 ml) at 0° C. (ice-water) under nitrogen was added camphorsulfonic acid (50 mg, 0.21 mmol) and the resulting mixture was stirred at about 0° C. for 2 hours. The mixture was concentrated in vacuo and the crude residue was used in the next step without purification. The desired product was obtained as a light yellow oil (707 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe crude residue was used in the next step without purification

Sources & evidence

ORD record
ord-1cb0eccbbc284b3cbab6a9beca6bd637
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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