Ethylene Oxide → 2-(Oxan-4-yloxy)ethan-1-ol

Temperature

0 °C

Into a 50-mL 3-necked round-bottom flask, was placed FeCl3 (800 mg, 4.94 mmol, 0.10 equiv). This was followed by the addition of oxan-4-ol (5 g, 48.96 mmol, 1.00 equiv) at 0° C. To this was added oxirane (20 mL) dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 2×50 mL of ethyl acetate and the organic layers combined. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:30-1:1). Purification afforded 2.25 g (crude) of 2-(oxan-4-yloxy)ethan-1-ol (54.2) as a colorless oil.

1. customInto a 50-mL 3-necked round-bottom flask, was placed
2. stirringThe resulting solution was stirred overnight at room temperature
3. customThe reaction was then quenched by the addition of 10 mL of water
4. extractionThe resulting solution was extracted with 2×50 mL of ethyl acetate
5. customPurification

ORD record

ord-ced0946a2b824c74ba8f91de36a343e9

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969557B2