Sulfuric Acid → Oleyl Alcohol

HRID 1156839Notes

Reaction equation

HRID 1156839 reaction equation
[C:1](O)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].OS(O)(=O)=O>CCOCC>[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 445639Oleic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 5284499Oleyl AlcoholYield 97.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of compound II (12 g) in 50 ml of dry ether was slowly dripped into a stirred suspension of 2 g of lithium aluminum hydride in 100 ml of dry ether. Gentle refluxing was maintained during addition, and the mixture was then refluxed for an additional 30 minutes. The mixture was chilled in an ice bath and treated gradually with 35 ml of ice water followed by 50 ml of cold 10% H2SO4. The ether layer was separated, the aqueous layer was shaken with two portions of ether, and the combined ether layers were dried over anhydrous Na2SO4. Evaporation of the solvent and distillation of the residue gave 11.1 g (97%) of compound III which boiled at 150° (0.02 mm), nD25 1.4608.

Workup

  1. temperatureGentle refluxing
  2. temperaturewas maintained during addition
  3. temperaturethe mixture was then refluxed for an additional 30 minutes
  4. temperatureThe mixture was chilled in an ice bath
  5. customThe ether layer was separated
  6. dry with materialthe combined ether layers were dried over anhydrous Na2SO4
  7. customEvaporation of the solvent and distillation of the residue

Sources & evidence

ORD record
ord-83c8413a92e2457cbe7774216be2d493
Source dataset
uspto-grants-1982_06
Patent number
US04337271

Reaction notes

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