Water → HCID 90781387, compound

HRID 1179092Notes

Reaction equation

HRID 1179092 reaction equation
O.[C:2]([C:10]([OH:12])=[O:11])(=[O:9])C1C=CC=CC=1.[CH2:13](O)[CH2:14][CH:15]=[CH2:16]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:10]([O:12][CH2:16][CH2:15][CH:14]=[CH2:13])(=[O:11])[CH:2]=[O:9]

Participants

6

Reactant 3

HCID 962WaterHCID 11915Phenylglyoxylic AcidHCID 693893-Buten-1-ol

Product 1

HCID 90781387HCID 90781387, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

In a flask with a water separator, a mixture of 11.02 g of benzoylformic acid (glyoxalic acid), 6.62 g of 3-buten-1-ol and 0.42 g of p-toluenesulfonic acid in 130 ml of toluene is heated at 110° C. for 22 hours. The solution is washed with saturated NaHCO3 solution and water. The organic phases are dried over sodium sulfate. Filtration, evaporation of the solvent and distillation (b.p.=85° C. at 0.035 mbar) give but-3-enyl glyoxalate (8.08 g, 54%) as a pale yellowish liquid.

Workup

  1. washThe solution is washed with saturated NaHCO3 solution and water
  2. dry with materialThe organic phases are dried over sodium sulfate
  3. filtrationFiltration, evaporation of the solvent and distillation (b.p.=85° C. at 0.035 mbar)

Sources & evidence

ORD record
ord-920574faa522455f9ac182bcb1817f3b
Source dataset
uspto-grants-2007_10
Patent number
US07279200B2

Reaction notes

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