1-Decanol → Decyl 2-hydroxyhexanoate

HRID 256797

Reaction equation

HRID 256797 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([OH:9])[C:6]([OH:8])=[O:7].[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>S(=O)(=O)(O)O>[OH:9][CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[C:6]([O:8][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:7]

Participants

4

Reactant 2

HCID 81741-DecanolHCID 998242-Hydroxyhexanoic acid

Product 1

HCID 19783884Decyl 2-hydroxyhexanoateYield 49%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
140 °C

Procedure

A 50 ml one neck round bottom flask equipped with a Dean Stark trap, condenser and a nitrogen inlet/outlet was charged with 5.0 g (0.038 moles) DL-2-hydroxycaproic acid, 23.95 g (0.151 moles) decyl alcohol, and 0.019 g sulfuric acid. The reactants were heated to 140° C. for 8 hours and water 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 4.34 g (49% yield) of clear colorless liquid. According to GC the product is 95.74% pure.

Workup

  1. customwater 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-07f892a4d3304c3596ab9f5fde776006
Source dataset
uspto-grants-1993_11
Patent number
US05260051

Linked notes

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