Ethylene Glycol → 2-((Benzyloxy)methyl)-2-methyl-1,3-dioxolane

HRID 31689

Reaction equation

HRID 31689 reaction equation
[CH2:1]([O:8][CH2:9][C:10](=[O:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13](O)[CH2:14][OH:15].C(OCC)(OCC)OCC>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>[CH2:1]([O:8][CH2:9][C:10]1([CH3:11])[O:15][CH2:14][CH2:13][O:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 31214Ethyl orthoformateHCID 36912841-(Benzyloxy)propan-2-one

Product 1

HCID 597925942-((Benzyloxy)methyl)-2-methyl-1,3-dioxolaneYield 90.5%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 1-benzyloxy-2-propanone (4.94 g, 30.1 mmol), ethylene glycol (20 ml, 359 mmol), triethyl orthoformate (5 ml, 30.1 mmol), and p-toluenesulfonic acid monohydrate (130 mg, 0.683 mmol) was stirred at room temperature for 61.5 hours. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution (20 ml) was added and the mixture was extracted twice with chloroform (50 ml) and the organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 4/1 gradient). Desired fractions were concentrated to obtain the title compound (5.67 g, 90.5% yield) as a colorless oil.

Workup

  1. extractionthe mixture was extracted twice with chloroform (50 ml)
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 4/1 gradient)
  5. concentrationDesired fractions were concentrated

Sources & evidence

ORD record
ord-4e1336d1e5884c6ca1ba3b640ca449a4
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

Loading…