1-Octanol → Octyl 2-hydroxypropanoate

HRID 2380178Notes

Reaction equation

HRID 2380178 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[CH:2]([CH3:4])[OH:3].[CH2:9](O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]CC>S(=O)(=O)(O)O>[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:5])[CH:2]([CH3:4])[OH:3]

Participants

4

Reactant 2

HCID 9571-OctanolHCID 7344Ethyl Lactate

Product 1

HCID 95499Octyl 2-hydroxypropanoateYield 44%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A 500 mL one neck round bottom flask equipped with a distillation apparatus and nitrogen inlet/outlet was charged with 100.0 g (0.85 moles) of ethyl lactate, 220.49 g (1.69 moles) of octyl alcohol and 0.42 g of sulfuric acid. The reaction was refluxed for 8 hours and ethanol was collected as formed. The acid was neutralized by washing three times with 100 mL saturated sodium bicarbonate solution. The organic layer was collected and dried over magnesium sulfate. Excess octyl alcohol was removed by high vacuum distillation, and three fractional distillations led to 75.0 g (44% yield) of clear colorless oil. According to GC, the product is 95% pure.

Workup

  1. temperatureThe reaction was refluxed for 8 hours
  2. customethanol was collected
  3. customas formed
  4. washby washing three times with 100 mL saturated sodium bicarbonate solution
  5. customThe organic layer was collected
  6. dry with materialdried over magnesium sulfate
  7. customExcess octyl alcohol was removed by high vacuum distillation, and three fractional distillations

Sources & evidence

ORD record
ord-4523dfe2942d4f478458165c8af42eb4
Source dataset
uspto-grants-1994_11
Patent number
US05366665

Reaction notes

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