Reaction #1189

Reaction equation

LiAlH4

methyl 12-hydroxyoctadecanate

KOH

→

1,12-octadecanediol

Yield 86.6%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   OtherA 5-liter flask equipped with a stirrer
2. 2
   Temperaturereflux tube
3. 3
   workup.ADDITIONwas added dropwise over 5 hours
4. 4
   TemperatureAfter the reaction mixture was then cooled
5. 5
   workup.STIRRINGwith stirring
6. 6
   OtherA salt precipitated
7. 7
   Otherwas separated by filtration
8. 8
   Concentrationthe resultant solution was concentrated under reduced pressure
9. 9
   OtherThe resulting residue was purified by column chromatography on silica gel

Procedure

A 5-liter flask equipped with a stirrer, dropping funnel and reflux tube was charged with 28.5 g (0.75 mol) of LiAlH4 and 2 liters of tetrahydrofuran, to which a solution of 237.0 g (0.75 mol) of methyl 12-hydroxyoctadecanate in 1 liter of tetrahydrofuran was added dropwise over 5 hours with stirring. After completion of the dropping, the stirring was continued further for 1 hour at 65° C. After the reaction mixture was then cooled, 90 ml of a 5% aqueous solution of KOH were added with stirring. A salt precipitated was separated by filtration, and the resultant solution was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel, thereby obtaining 185.7 g (yield: 86.6%) of 1,12-octadecanediol.

Source