Ethylene Glycol → 2-(2-(Benzyloxy)ethyl)-2-methyl-1,3-dioxolane
Reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11](=[O:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14](O)[CH2:15][OH:16].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][CH2:10][C:11]1([CH3:12])[O:16][CH2:15][CH2:14][O:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
6
Procedure
A mixture of 4-benzyloxy-2-butanone (10 g, 56.1 mmol), ethylene glycol (40 ml, 718 mmol), triethyl orthoformate (9.3 ml, 55.9 mmol) and p-toluenesulfonic acid monohydrate (290 mg, 1.52 mmol) was stirred at room temperature for 13.5 hours. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution (40 ml) was added and the mixture was extracted three times with chloroform (50 ml). 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 (10.08 g, 80.8% yield) as a colorless oil.
Workup
- extractionthe mixture was extracted three times with chloroform (50 ml)
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 4/1 gradient)
- concentrationDesired fractions were concentrated
Sources & evidence
- ORD record
- ord-547e069fc65a4671b006b58491a3d950
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124780B2
Reaction notes
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