1-Decanol → Decyl 2-Hydroxyoctanoate

HRID 256798Notes

Reaction equation

HRID 256798 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 77.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A 250 ml one neck round bottom flask equipped with a Dean Stark trap, condenser and nitrogen inlet/outlet was charged with 20.0 g (0.125 moles) 2-hydroxyoctanoic acid, 79.0 g (0.499 moles) decyl alcohol, and 0.062 g sulfuric acid. The mixture was heated to 140° 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 28.99 g (77.3% yield) of clear pale yellow liquid. According to GC the product is 99.6% pure.

Workup

  1. temperatureThe mixture was heated to 140° for 8 hours
  2. customwater was collected as the reaction
  3. washby washing three times with 50 ml saturated sodium bicarbonate solution
  4. customThe organic layer was collected
  5. dry with materialdried over magnesium sulfate
  6. customExcess decyl alcohol was removed by high vacuum distillation

Sources & evidence

ORD record
ord-b00d648aea424b888fe4c5c262f9d621
Source dataset
uspto-grants-1993_11
Patent number
US05260051

Reaction notes

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