1,5-Pentanediol → HCID 67321917, compound

Participants

Reaction Conditions

Reaction Steps

1,5-Pentanediol (1,171 g (11.2 mol)), tetrabutylammonium bromide (24.1 g (75 mmol)) and 96% sodium hydroxide (90 g (2.2 mol)) were added to a glass flask having an inner volume of 2,000 ml equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser, and the mixture was warmed to 70° C. with stirring. Subsequently 3-ethyl-3-methanesulfonyloxymethyloxetane (324 g (1.5 mol)) having a purity of 90% (a value measured by 1H-NMR) was dropwise added while keeping the liquid temperature at 75-85° C. to perform the reaction at the same temperature for 3 hours. After the completion of the reaction, the reaction solution was washed with heptane (200 ml), and then water (583 ml) was added and a liquid separation was performed. Water (1,166 ml) and toluene (500 ml) were added to a resultant organic layer, and a liquid separation was performed. Subsequently toluene (500 ml) was added to a resultant aqueous layer to perform the extraction, an extract (a toluene layer) and an organic layer were mixed, and a resultant mixture was washed at water (300 ml). Subsequently a resultant aqueous layer and an aqueous layer separated earlier were mixed, and a resultant mixture was extracted with toluene (500 ml). After washing an extract (a toluene layer) with water (300 ml), the extract was mixed with the previously obtained organic layer, and a resultant mixture was concentrated under reduced pressure. A resultant concentrate (a bisoxetane ether compound generated in the amount of only 14% (an analysis value by a gas chromatography)) was distilled under reduced pressure (136-140° C., 533 Pa) to give, as a colorless liquid, 3-ethyl-3-(5-hydroxypentyl)oxymethyloxetane having a purity of 93% (an analysis value by a gas chromatography) (109 g) (an isolated yield based on 3-ethyl-3-methanesulfonyloxymethyloxetane: 33%).

Provenance & Evidence