Lactic Acid → Octyl 2-hydroxypropanoate

HRID 256793Notes

Reaction equation

HRID 256793 reaction equation
[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[CH2:7](O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[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

5

Reactant 3

HCID 612Lactic AcidHCID 9571-OctanolHCID 1118Sulfuric Acid

Product 1

HCID 95499Octyl 2-hydroxypropanoateYield 35.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 2 liter one neck round bottom flask equipped with a Dean Stark trap, condenser and nitrogen, inlet outlet was charged with 150.0 g (1.66 moles) lactic acid, 293.0 g (2.25 moles) octyl alcohol, 6 ml sulfuric acid and 500 ml toluene. Mixture was heated to 130° for 2.5 hours and water was collected as the reaction proceeded. The acid was neutralized by washing three times with 50 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. Octyl lactate was distilled under high vacuum to yield 119.85 g (35.6% yield) of clear colorless liquid. According to GC the product is 96.2% pure.

Workup

  1. temperatureMixture was heated to 130° for 2.5 hours
  2. customwater was collected as the reaction
  3. washby washing three times with 50 ml saturated sodium bicarbonate solution
  4. customThe organic layer was collected
  5. dry with materialdried over magnesium sulfate
  6. distillationOctyl lactate was distilled under high vacuum

Sources & evidence

ORD record
ord-12de98b0c10749cd9731aa5b85bad87e
Source dataset
uspto-grants-1993_11
Patent number
US05260051

Reaction notes

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