Diethyl Ether → 2-Cyclohexylacetaldehyde

A suspension of 100 g (0.46 moles) of pyridinium chlorochromate and 100 g of celite in 800 ml of methylene chloride was stirred vigorously while 38 g (0.3 moles) of 2-cyclohexylethanol in 200 ml of methylene chloride was added all at once. The reaction turned dark immediately and became mildly exothermic. After 1 hour, 1000 ml of ether was added and the reaction mixture was filtered through a bed of silica gel (ca. 250 g) on a fritted glass disk. The pad was rinsed with an additional liter of ether. The combined filtrates were reduced in volume to approximately 200 ml and the solution was washed with 2×40 ml of 6N HCl, 1×50 ml of saturated sodium bicarbonate, and 1×50 ml of saturated NaCl solution. The organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo to give a light green oil. The residue was distilled in vacuo to afford 21 g (56%) of a colorless oil (bp 74°-76° C. at 23 mm of Hg).

1. additionwas added all at once
2. filtrationthe reaction mixture was filtered through a bed of silica gel (ca. 250 g) on a fritted glass disk
3. washThe pad was rinsed with an additional liter of ether
4. washthe solution was washed with 2×40 ml of 6N HCl, 1×50 ml of saturated sodium bicarbonate, and 1×50 ml of saturated NaCl solution
5. dry with materialThe organic layer was dried over magnesium sulfate
6. filtrationfiltered
7. customevaporated in vacuo
8. customto give a light green oil
9. distillationThe residue was distilled in vacuo

ORD record

ord-3aaf3f9990fa43229d2a47b5474dc484

Source dataset

uspto-grants-1992_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05145990