Trimethyl orthoformate → (2-Methoxy-1,3-dioxan-5-yl)methanol

HRID 1645531Notes

Reaction equation

HRID 1645531 reaction equation
[OH:1][CH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].[CH:8](OC)(OC)[O:9][CH3:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(N(CC)CC)C>[CH3:8][O:9][CH:10]1[O:5][CH2:4][CH:3]([CH2:6][OH:7])[CH2:2][O:1]1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 78432TrimethylolmethaneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 59792360(2-Methoxy-1,3-dioxan-5-yl)methanolYield 59.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 2-(hydroxymethyl)-1,3-propanediol (1.7 g, 16 mmol), trimethyl orthoformate (7 ml, 64.1 mmol), and p-toluenesulfonic acid monohydrate (275 mg, 1.6 mmol) was stirred at room temperature for 22 hours. To the reaction mixture, triethylamine (447 μl) was added and the mixture was concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to obtain the title compound (1.4 g, 59.1% yield), which is a cis and trans (1:1) mixture, as a light yellow oil.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate)

Sources & evidence

ORD record
ord-fea9f0555e274121ab407af2aea5f0c6
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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