1-Decanol → Decyl lactate

HRID 256794

Reaction equation

HRID 256794 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[CH:2]([CH3:4])[OH:3].[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]C.[OH-].[Na+]>OS(O)(=O)=O.CO>[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:5])[CH:2]([CH3:4])[OH:3]

Participants

6

Reactant 3

HCID 81741-DecanolHCID 11040Methyl LactateHCID 14798Sodium Hydroxide

Product 1

HCID 347720Decyl lactateYield 180.9%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

A 250 mL round bottom flask equipped with a spin bar and a distillation column was charged with 100 g (0.96 moles) of methyl lactate, 304.1 g (1.92 moles) of decyl alcohol, and 500 mg of H2SO4. The reaction was heated until methanol formation ceased. The reaction was then neutralized with 0.1N NaOH (100 mL) and extracted with ether. The organic layer was dried over MgSO4, filtered and dried in vacuo to give 400 g of crude mixture. The fractional distillation was carried out three times to give 98.5 g (45% yield, 100% pure by GC) of a clear colorless oil.

Workup

  1. customA 250 mL round bottom flask equipped with a spin bar
  2. distillationa distillation column
  3. extractionextracted with ether
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2f1662f043fa4ee182792689b288e74b
Source dataset
uspto-grants-1993_11
Patent number
US05260051

Linked notes

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