Methyl linoleate → Linoleyl alcohol

HRID 2351955Notes

Reaction equation

HRID 2351955 reaction equation
[C:1](OC)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 5284421Methyl linoleateHCID 21226445Aluminium lithium hydride

Product 1

HCID 5365682Linoleyl alcoholYield 97.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 20.0 g of methyl linoleate in 20 ml of diethyl ether was added to a suspension of 1.8 g of lithium aluminum hydride in 150 ml of diethyl ether at approximately 0° C. under an argon atmosphere. The mixture was stirred for approximately 2 hours at 0° C. The reaction was quenched by the slow addition of 1.8 ml of water, followed by 1.8 ml of 15% sodium hydroxide and 5.4 ml of water. The mixture was filtered and the filtrate was evaporated to dryness. The resulting oil was dissolved in diethyl ether, washed with water, dried over magnesium sulfate, filtered, and evaporated to provide 17.7 g of linoleyl alcohol.

Workup

  1. customThe reaction was quenched by the slow addition of 1.8 ml of water
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe resulting oil was dissolved in diethyl ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-f34364e52eff4e2aa59753b7be2971bf
Source dataset
uspto-grants-1989_10
Patent number
US04874782

Reaction notes

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