Methyl 12-hydroxystearate → Hydroxystearyl alcohol

HRID 1093

Reaction equation

HRID 1093 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH:8]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](OC)=[O:20].[OH-].[K+]>O1CCCC1>[CH2:19]([OH:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:8]([OH:7])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 8840Methyl 12-hydroxystearateHCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 95421Hydroxystearyl alcoholYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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.

Workup

  1. customA 5-liter flask equipped with a stirrer
  2. temperaturereflux tube
  3. additionwas added dropwise over 5 hours
  4. temperatureAfter the reaction mixture was then cooled
  5. stirringwith stirring
  6. customA salt precipitated
  7. customwas separated by filtration
  8. concentrationthe resultant solution was concentrated under reduced pressure
  9. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9598dbc5228f4c2bae79065911c76e2b
Source dataset
uspto-grants-1998_03
Patent number
US05723497

Linked notes

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