Stearyl Alcohol → HCID 18914774, compound

HRID 1179094Notes

Reaction equation

HRID 1179094 reaction equation
[C:1]([C:9](O)=[O:10])(=[O:8])C1C=CC=CC=1.[CH2:12]([OH:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:9]([O:30][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:10])[CH:1]=[O:8]

Participants

6

Reactant 3

HCID 8221Stearyl AlcoholHCID 11915Phenylglyoxylic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 18914774HCID 18914774, compoundYield 162.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 5 g of benzoylformic acid (glyoxalic acid), 11.3 g of octadecanol and 0.19 g of p-toluenesulfonic acid in 60 ml of toluene is heated at reflux for 22 hours. The mixture is poured into saturated NaHCO3 solution and the phases are separated. The organic phases are washed with water and dried over sodium sulfate. Filtration and evaporation of the solvent give octadecyl glyoxalate (17.7 g) as a yellow solid. The product is recrystallized from methanol to give slightly yellowish crystals (11.29 g, 84%).

Workup

  1. temperatureat reflux for 22 hours
  2. customthe phases are separated
  3. washThe organic phases are washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-91c011aeaf1648c9818c3d80586edcf4
Source dataset
uspto-grants-2007_10
Patent number
US07279200B2

Reaction notes

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