Sodium Sulfate → HCID 57429404, compound

Temperature

0 °C

LiAlH4 (16 g, 0.42 mol, 1.2 eq) and diethyl ether (450 mL) were charged into a 2 L three-necked round-bottom flask equipped with a mechanical stirrer and a reflux condenser and cooled at 0° C. The crude 3-(3-methylcyclohexyl)propanoic acid (60 g, 0.35 mol) was dissolved in diethyl ether (400 mL) and added dropwise to the reaction flask. The reaction mixture was then stirred for 3 h at ambient temperature. The excess of lithium aluminium hydride was hydrolyzed with saturated aqueous sodium sulphate and the mixture filtered. THF (1 L) was added to the residue and the suspension was heated to 35° C. for 1 h. The suspension was filtered and the combined organic layers were dried over sodium sulphate and evaporated to yield the crude product as an oil. Chromatography on a silica gel column with 8% EtOAc in hexane as elution agent, followed by a bulb-to-bulb distillation (0.1 mBar, 140° C.) gave pure 3-(3-methylcyclohexyl)propan-1-ol (35 g, gc purity>98%; yield=61%).

1. customequipped with a mechanical stirrer and a reflux condenser
2. additionadded dropwise to the reaction flask
3. filtrationthe mixture filtered
4. additionTHF (1 L) was added to the residue
5. temperaturethe suspension was heated to 35° C. for 1 h
6. filtrationThe suspension was filtered
7. dry with materialthe combined organic layers were dried over sodium sulphate
8. customevaporated
9. customto yield the crude product as an oil
10. washChromatography on a silica gel column with 8% EtOAc in hexane as elution agent
11. distillationfollowed by a bulb-to-bulb distillation (0.1 mBar, 140° C.)

ORD record

ord-d3a0fae7648f4f2b968bbcd0eb9bed62

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08709994B2