p-Toluenesulfonic acid → 8-(3-Methylpentyloxy)octanol

To a solution of 1.67 gms of 3-methyl pentanol in 40 ml of dimethylformamide, 0.62 gms of sodium hydride are added; and the reaction mixture is stirred at room temperature for 1 hour. To this solution is added 4.0 gms of the protected bromo-alcohol and the reaction mixture is stirred at room temperature for 17 hours. The reaction mixture is then partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to give a yellow liquid. To a solution of 4.0 gms of this liquid in 240 ml of methanol is added 0.40 gms of p-toluenesulfonic acid and the reaction is stirred at room temperature for 16 hours. The methanol is removed under reduced pressure, and the residue is partitioned between ethyl acetate and water. The organic layer is washed with aqueous NaHCO3 and brine, then dried over Na2SO4, filtered, and concentrated under vacuum to give 8-(3-methylpentyloxy)octanol.

1. stirringthe reaction mixture is stirred at room temperature for 17 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 Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customto give a yellow liquid
8. stirringthe reaction is stirred at room temperature for 16 hours
9. customThe methanol is removed under reduced pressure
10. customthe residue is partitioned between ethyl acetate and water
11. washThe organic layer is washed with aqueous NaHCO3 and brine
12. dry with materialdried over Na2SO4
13. filtrationfiltered
14. concentrationconcentrated under vacuum

ORDレコード

ord-4365ea31456546e198c66696939c2a4c

出典データセット

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05412137