Diethyl octylmalonate → 2-Octylpropane-1,3-diol

Borane methyl sulfide (BMS) complex (80 g, 1 m) was added dropwise to a mixture of diethyl-n-octylmalonate (90 g, 0.33) and tolune (400 ml) with stirring at room temperature. Stirring was continued for an additional hour. The mixture was refluxed gently for 10 hours, cooled to 20° C., and then poured slowly into ice-cold methanol (400 ml) with stirring and left to stand overnight. The solvent was stripped off and the residue was stirred with 10% hydrochloric acid solution (400 ml) overnight. The resulting mixture was extracted with chloroform (2×70 ml) and washed with water until neutral to litmus. The solvent was evaporated and the residue was vacuum distilled to yield 2-n-octylpropane-1,3-diol (25.5 g, 41%) bp 135°-140° C./0.5-0.8 mm.

1. stirringStirring
2. waitwas continued for an additional hour
3. temperatureThe mixture was refluxed gently for 10 hours
4. temperaturecooled to 20° C.
5. stirringwith stirring
6. waitleft
7. extractionThe resulting mixture was extracted with chloroform (2×70 ml)
8. washwashed with water until neutral to litmus
9. customThe solvent was evaporated
10. distillationdistilled

ORD record

ord-164aeeb371254c0ab6bf951732053e6a

Source dataset

uspto-grants-1980_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04200580