Ethanol → HCID 53961628, compound

HRID 1756317Notes

Reaction equation

HRID 1756317 reaction equation
[CH:1]([O:3][CH2:4][CH:5](O)[CH:6]=[CH2:7])=[O:2].C([C:11](CC)(CC)[C:12]([O-:15])([O-:14])[O-])C.[CH2:20](O)[CH3:21]>C(O)(=O)CC>[CH:1]([O:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:11][C:12]([O:14][CH2:20][CH3:21])=[O:15])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 10909540HCID 10909540, compoundHCID 21875354Triethylorthoaceate

Product 1

HCID 53961628HCID 53961628, compound

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidCatalyst

Procedure

A solution of 4-formyloxy-3-hydroxy-1-butene (1.06 g, 10 mmol) and propionic acid (1 drop) in triethylorthoacetate (6 g, 40 mmol) was heated at 140° C. under conditions for distillative removal of ethanol. After 2 H, the excess of ethylorthoacetate was removed by distillation in vacuo. The residue was hydrolysed with water and extracted with AcOEt. The product was purified by flash chromatography on SiO2 (eluant AcOEt: hexane, 2:8) (1 g, 60%) but distillative purification is preferred when larger quantities are involved.

Workup

  1. customAfter 2 H, the excess of ethylorthoacetate was removed by distillation in vacuo
  2. extractionextracted with AcOEt
  3. distillationThe product was purified by flash chromatography on SiO2 (eluant AcOEt: hexane, 2:8) (1 g, 60%) but distillative purification

Sources & evidence

ORD record
ord-f74ae7fcc3a541c09d097aeb2ba4f51b
Source dataset
uspto-grants-1995_08
Patent number
US05440065

Reaction notes

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