1-Decanol → Decyl 2-Hydroxyoctanoate

HRID 2380183Notes

Reaction equation

HRID 2380183 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([OH:5])=[O:4].[CH2:12](O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>S(=O)(=O)(O)O>[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([O:5][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:4]

Participants

4

Reactant 2

HCID 81741-DecanolHCID 94180Hydroxycaprylic Acid

Product 1

HCID 18955021Decyl 2-HydroxyoctanoateYield 80.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
140 °C

Procedure

A 250 mL one neck round bottom flask equipped with a Dean Stark trap, condensor and nitrogen inlet/outlet was charged with 20.0 g (0.12 moles) 2-hydroxyoctanoic acid, 79.0 g (0.50 moles) decyl alcohol, and 624 mg sulfuric 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. The organic layer was collected and dried over magnesium sulfate. Excess decyl alcohol was removed by high vacuum distillation to yield 28.99 g (77.3% yield) of clear pale yellow liquid. According to GC the product is 95.0% 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-3dea21c8a8914c2aa40d676f5ac30cdd
Source dataset
uspto-grants-1994_11
Patent number
US05366665

Reaction notes

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