5-Hexen-1-ol → HCID 86590220, compound

HRID 1179091Notes

Reaction equation

HRID 1179091 reaction equation
C[C:2](=[O:6])[C:3]([OH:5])=[O:4].[C:7]([C:15](OC)=O)(=O)[C:8]1C=C[CH:11]=[CH:10][CH:9]=1.C(O)CCCC=C>C1(C)C=CC(S(O)(=O)=O)=CC=1.CO>[C:3]([O:5][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]=[CH2:15])(=[O:4])[CH:2]=[O:6]

Participants

5

Reactant 2

HCID 699635-Hexen-1-olHCID 86590221HCID 86590221, compound

Product 1

HCID 86590220HCID 86590220, compoundYield 147.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 25 g of methyl benzoylformate (methyl glyoxalate), 15.25 g of 5-hexen-1-ol and 1.02 g of p-toluenesulfonic acid is heated at 120° C. for 18 hours. The methanol formed is removed by distillation. The mixture is poured into water (70 ml) and extracted with ethyl acetate. The organic phases are washed with water and dried over magnesium sulfate. Filtration, evaporation of the solvent, chromatography (eluent: 3:1 hexanethyl acetate) and distillation (b.p.=115° C. at 0.006 mbar) give hex-5-enyl glyoxalate (22.8 g, 64%) as a pale yellowish liquid.

Workup

  1. customis removed by distillation
  2. additionThe mixture is poured into water (70 ml)
  3. extractionextracted with ethyl acetate
  4. washThe organic phases are washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration, evaporation of the solvent, chromatography (eluent: 3:1 hexanethyl acetate) and distillation (b.p.=115° C. at 0.006 mbar)

Sources & evidence

ORD record
ord-3c4be9a1c80a481db32bf395cc27cfb9
Source dataset
uspto-grants-2007_10
Patent number
US07279200B2

Reaction notes

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