1,4-Butanediol → 4-Nonyloxybutanol

To a solution of 7.1 ml of 1,4-butanediol in 40 ml of dimethylformamide, 1.8 gms of sodium hydride are added; and the reaction mixture is stirred at room temperature for 15 minutes. To this solution is added 7.6 ml of bromononane and the reaction mixture is stirred at room temperature for 44 hours. The reaction mixture is then partitioned between ethyl acetate and water and the organic layer is washed with brine, dried over sodum sulfate, filtered, and concentrated under vacuum. The residue is flash chromatographed with an 8/1 ratio of ethyl acetate and hexane to give 4-nonyloxybutanol as a clear colorless liquid.

1. stirringthe reaction mixture is stirred at room temperature for 44 hours
2. customThe reaction mixture is then partitioned between ethyl acetate and water
3. washthe organic layer is washed with brine
4. dry with materialdried over sodum sulfate
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customchromatographed with an 8/1 ratio of ethyl acetate and hexane

ORD record

ord-8fcbf24c14134cb69e55f6d2d3b5797c

Source dataset

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05412137