Lactic Acid → Decyl lactate

HRID 2380180

Reaction equation

HRID 2380180 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][CH2:14][CH2:15][CH3:16].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][CH2:14][CH2:15][CH3:16])(=[O:5])[CH:2]([CH3:4])[OH:3]

Participants

5

Reactant 3

HCID 612Lactic AcidHCID 1118Sulfuric AcidHCID 81741-Decanol

Product 1

HCID 347720Decyl lactateYield 13.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
145 °C

Procedure

A 500 mL one neck round bottom flask equipped with a Dean Stark trap, condensor and nitrogen inlet/outlet was charged with 22.52 g (0.75 moles) lactic acid, 47.46 g (0.98 moles) decyl alcohol, 3 ml sulfuric acid and 220 mL toluene. The mixture was heated to 145° C. for 20 hours and water was collected as the reaction proceeded. The acid was neutralized by washing three times with 50 ml saturated sodium bicarbonate solution. The organic layer was collected and dried over magnesium sulfate. Decyl lactate was distilled under high vacuum to yield 24.03 g (12.4% yield) of clear colorless liquid. According to GC the product is 97.78% pure.

Workup

  1. customwater was collected as the reaction
  2. washby washing three times with 50 ml saturated sodium bicarbonate solution
  3. customThe organic layer was collected
  4. dry with materialdried over magnesium sulfate
  5. distillationDecyl lactate was distilled under high vacuum

Sources & evidence

ORD record
ord-cac6b32a9613412f9ee0a7b67ba8453b
Source dataset
uspto-grants-1994_11
Patent number
US05366665

Linked notes

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