1-Octanol → Octyl 2-hydroxypropanoate

HRID 256792Notes

Reaction equation

HRID 256792 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 3

HCID 9571-OctanolHCID 1118Sulfuric AcidHCID 7344Ethyl Lactate

Product 1

HCID 95499Octyl 2-hydroxypropanoateYield 44%

Procedure

A 500 mL one neck round bottom flask equipped with a distillation apparatus and nitrogen inlet/outlet was charged with 100.0 g (0.847 moles) of ethyl lactate, 220.49 g (1.69 moles) of octyl alcohol and 0.423 g of sulfuric acid (based on 0.5 g sulfuric acid/one mole ethyl lactate). 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. Approximately 50 mL ether was needed to break the emulsion. 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-f42ee048b59c4ef4b9e358aa8939591c
Source dataset
uspto-grants-1993_11
Patent number
US05260051

Reaction notes

Loading…