Hydrochloric Acid → 6-(Tetrahydro-2H-pyran-2-yloxy)-1-hexanol

Hexane-1,6-diol (70.9 g) was melted in a water bath at ca. 60°, the melt cooled to 45° and dihydropyran (16.82 g) quickly added followed by 10 N hydrochloric acid (0.1 ml). The mixture was stirred and cold water added to maintain a reaction temperature of approximately 50°. When the exotherm had subsided, the mixture was stirred at room temperature for 0.5 h, then diluted with water (500 ml) and extracted with ER (2×250 ml). The ER solution was washed with water (3×500 ml), dried and concentrated to yield an oil which was purified by [FCS] elution with EA/hexane (1:1) affording the title compound (19.6 g). T.l.c. (EA/hexane 1:1) Rf 0.40.

1. temperaturethe melt cooled to 45°
2. temperatureto maintain a reaction temperature of approximately 50°
3. stirringthe mixture was stirred at room temperature for 0.5 h
4. extractionextracted with ER (2×250 ml)
5. washThe ER solution was washed with water (3×500 ml)
6. customdried
7. concentrationconcentrated
8. customto yield an oil which
9. customwas purified by [FCS] elution with EA/hexane (1:1)

ORD record

ord-aa6c4d51ade24574bf8f25f5f013a26b

Source dataset

uspto-grants-1991_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04990505