3-Hydroxybutyric Acid → Decyl 3-hydroxybutanoate

HRID 256796Notes

Reaction equation

HRID 256796 reaction equation
[OH:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>S(=O)(=O)(O)O>[OH:1][CH:2]([CH3:7])[CH2:3][C:4]([O:6][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:5]

Participants

4

Reactant 2

HCID 4413-Hydroxybutyric AcidHCID 81741-Decanol

Product 1

HCID 18955013Decyl 3-hydroxybutanoateYield 58%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
140 °C

Procedure

A 100 ml one neck round bottom flask equipped with a Dean Stark trap, condenser and nitrogen inlet/outlet was charged with 20.8 g (0.20 moles) 3-hydroxybutyric acid, 63.3 g (0.40 moles) decyl alcohol, and 0.1 g sulfuric acid (based on 0.5 g/mole 3-hydroxybutyric acid). The mixture was heated to 140° C. for 8 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. Excess decyl alcohol was removed by high vacuum distillation to yield 28.3 g (58% yield) of clear viscous colorless oil. According to GC the product is 89.4% 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. customExcess decyl alcohol was removed by high vacuum distillation

Sources & evidence

ORD record
ord-455d0015f18a471f8d6cd93cf4c68d19
Source dataset
uspto-grants-1993_11
Patent number
US05260051

Reaction notes

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