Reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12](O)[CH2:13][OH:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH:10]1[O:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 140 °C
Procedure
A mixture of benzyloxyacetaldehyde (3 g, 20 mmol), ethylene glycol (1.23 ml, 22 mmol), p-toluenesulfonic acid monohydrate (344 mg, 1.8 mmol), and toluene (15 ml) was stirred at 140° C. for 2 hours and further stirred at 150° C. for 3 hours. After cooled on ice, a 2N aqueous sodium hydroxide solution and ethyl acetate were added to the reaction mixture. An organic layer was separated, washed with water (three times) and a saturated saline solution. 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 9/1 gradient). Desired fractions were concentrated to obtain the title compound (3.01 g, 77.5% yield) as a light yellow oil.
Workup
- stirringfurther stirred at 150° C. for 3 hours
- temperatureAfter cooled on ice
- customAn organic layer was separated
- washwashed with water (three times)
- 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 9/1 gradient)
- concentrationDesired fractions were concentrated
Sources & evidence
- ORD record
- ord-3cf244367dc94f98812ae6228bd6bf02
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07425634B2
Linked notes
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