12-羟基硬脂酸甲酯 → 1,12-十八烷二醇

HRID 1093

反应方程式

HRID 1093 反应方程式
[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]

参与物

5

反应物 3

HCID 884012-羟基硬脂酸甲酯HCID 14797氢氧化钾HCID 21226445Aluminium lithium hydride

产物 1

HCID 954211,12-十八烷二醇收率 86.6%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-9598dbc5228f4c2bae79065911c76e2b
来源数据集
uspto-grants-1998_03
专利号
US05723497

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