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

HRID 31592

Reaction equation

HRID 31592 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-900281ff6a674c459015a992c92073ad
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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