Acetic Acid → 1-Isooctyl-3-methyl glycerol

HRID 1645750Notes

Reaction equation

HRID 1645750 reaction equation
[Na].CO.[CH2:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:5]1[O:7][CH2:6]1.[C:17](O)(=[O:19])C>>[CH2:9]([O:8][CH2:4][CH:5]([CH2:6][O:19][CH3:17])[OH:7])[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 5360545SodiumHCID 22571168Oxirane, 2-[[(6-methylheptyl)oxy]methyl]-

Product 1

HCID 198021661-Isooctyl-3-methyl glycerol

Procedure

Sodium metal (2.3 g; 0.1 mole) is dissolved in methanol (160 g; 5 moles). The solution is heated to reflux and treated dropwise over 2 hours with isooctyl glycidyl ether (186 g; 1 mole). After complete addition, the reaction mixture is maintained under reflux conditions for a further 6 hours. After cooling to ambient temperature, the reaction mixture is treated with acetic acid (5.8 g; 0.1 mole) and then the excess solvent is removed under vacuum. The oily residue is treated with water (250 ml) and then extracted with ether (250 ml). The ether extract is dried over MgSO4, filtered and evaporated. The residue is distilled under vacuum to yield 1-isooctyl-3-methyl glycerol, as a colourless oil, bp 75°-80° C./0.07 mbar, yield 145.6 g (67%).

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux
  3. additionAfter complete addition
  4. temperaturethe reaction mixture is maintained under reflux conditions for a further 6 hours
  5. customthe excess solvent is removed under vacuum
  6. additionThe oily residue is treated with water (250 ml)
  7. extractionextracted with ether (250 ml)
  8. extractionThe ether extract
  9. dry with materialis dried over MgSO4
  10. filtrationfiltered
  11. customevaporated
  12. distillationThe residue is distilled under vacuum

Sources & evidence

ORD record
ord-172b8286fe454cc6970af564be973042
Source dataset
uspto-grants-1993_01
Patent number
US05176850

Reaction notes

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