3-Hydroxybutyric Acid → Dodecyl 3-Hydroxybutyrate

HRID 2380182Notes

Reaction equation

HRID 2380182 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>>[OH:1][CH:2]([CH3:7])[CH2:3][C:4]([O:6][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8])=[O:5]

Participants

4

Reactant 3

HCID 4413-Hydroxybutyric AcidHCID 1118Sulfuric AcidHCID 81931-Dodecanol

Product 1

HCID 18955122Dodecyl 3-HydroxybutyrateYield 117.65%

Conditions

Temperature
120 °C

Procedure

A 500 mL one neck round bottom flask equipped with a Dean Stark trap, condenser, and a nitrogen inlet/outlet was charged with 72.0 g (69 mmole) of 3-hydroxybutyric acid, 268.5 g (1.45 mole) of dodecyl alcohol, and 0.36 g of sulfuric acid. The mixture was heated to 120° C. for 48 hours and water was collected as the reaction proceeded. The acid was neutralized by washing three times with 100 mL saturated NaHCO3 solution. The organic layer was collected and dried over MgSO4 and concentrated. Excess dodecanol was removed by high vacuum distillation to yield 117.65% (60% yield) of clear oil (91% pure by GC).

Workup

  1. customwater was collected as the reaction
  2. washby washing three times with 100 mL saturated NaHCO3 solution
  3. customThe organic layer was collected
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customExcess dodecanol was removed by high vacuum distillation

Sources & evidence

ORD record
ord-42787cf725b047e0bc59a10aa1987dc9
Source dataset
uspto-grants-1994_11
Patent number
US05366665

Reaction notes

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