Acetic Anhydride → HCID 178476339, compound

To a mixture of trans-4-(hydroxymethyl)cyclohexanol (1.8 g, 14 mmol, Tetrahedron Lett. 1970, 11, 4281-4284.), triethylamine (2.4 mL, 17 mmol), and N,N-dimethylaminopyridine (0.34 g, 3.0 mmol) in tetrahydrofuran (70 mL) was added acetic anhydride (1.4 mL, 15 mmol) at room temperature. After being stirred at room temperature for 48 h, the mixture was concentrated in vacuo to give an oil. The residual oil was extracted with ethyl acetate (100 mL). The organic layer was washed with successively 2N hydrochloric acid, aq. sodium hydrogencarbonate, and brine. The extract was dried over magnesium sulfate and concentrated in vacuo give an oil. The residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 1:1 to 1:2) to give 1.2 g (50%) the title compound as a colorless oil.

1. concentrationthe mixture was concentrated in vacuo
2. customto give an oil
3. extractionThe residual oil was extracted with ethyl acetate (100 mL)
4. washThe organic layer was washed with successively 2N hydrochloric acid, aq. sodium hydrogencarbonate, and brine
5. dry with materialThe extract was dried over magnesium sulfate
6. concentrationconcentrated in vacuo
7. customgive an oil
8. customThe residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 1:1 to 1:2)

ORD record

ord-6fc30a57894b4bc993f61c222f9382f1

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08816090B2