3-Hydroxybutyric Acid → Dodecyl 3-Hydroxybutyrate

HRID 256799Notes

Reaction equation

HRID 256799 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][CH2:17][CH2:18][CH3:19]>S(=O)(=O)(O)O>[CH2:19]([O:5][C:4](=[O:6])[CH2:3][CH:2]([OH:1])[CH3:7])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8]

Participants

4

Reactant 2

HCID 4413-Hydroxybutyric AcidHCID 81931-Dodecanol

Product 1

HCID 18955122Dodecyl 3-HydroxybutyrateYield 62.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A 500 ml one neck round bottom flask equipped with a Dean Stark trap, condenser and nitrogen inlet/outlet was charged with 72.0 g (0.69 moles) 3- hydroxybutyric acid, 268.5 g (1.45 moles) dodecyl alcohol, and 0.36 g sulfuric acid (based on 0.5 g/mole 3-hydroxybutyric acid). The mixture was heated to 115 degrees for 48 hours and water was collected as the reaction proceeded. 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 dodecyl alcohol was removed by high vacuum distillation to yield 117.65 g (60% yield) of clear oil (91% pure by GC).

Workup

  1. temperatureThe mixture was heated to 115 degrees for 48 hours
  2. customwater was collected as the reaction
  3. washby washing three times with 100 ml saturated sodium bicarbonate solution
  4. customThe organic layer was collected
  5. dry with materialdried over magnesium sulfate
  6. customExcess dodecyl alcohol was removed by high vacuum distillation

Sources & evidence

ORD record
ord-a47b2d80e9cc48ca9fbd823d760c630e
Source dataset
uspto-grants-1993_11
Patent number
US05260051

Reaction notes

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