Propionic Acid → HCID 14786682, compound

HRID 373424Notes

Reaction equation

HRID 373424 reaction equation
[CH2:1]([C:3](CC)(CC)C([O-])([O-])[O-])[CH3:2].[C:12]([OH:16])(=[O:15])[CH2:13][CH3:14].[CH3:17][C:18](=CC)CO.[C:23]([O-])(=O)C=CCC>>[CH3:23][CH:14]([C:1]([CH3:3])=[CH2:2])[CH2:13][C:12]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 4

HCID 1032Propionic AcidHCID 207992-Methylbut-2-enolHCID 21875354TriethylorthoaceateHCID 53400757HCID 53400757, compound

Product 1

HCID 14786682HCID 14786682, compoundYield 41%

Procedure

In a 3 l flask equipped with a mechanical stirrer and a condenser, kept under nitrogen, a mixture of triethylorthoacetate (1117.8 g), propionic acid (2.3 g) and 2-methyl-2-buten-1-ol (59.3 g) was heated at 118° for 72 h in order to distil the ethanol gradually as it was formed. The excess of triethylorthoacetate was recovered and the distillation was completed under reduced pressure. The raw product thus obtained (69.0 g) contained around 80% of the desired pentenoate. Purification on a Fischer column yielded 43.7 g (41%) of ethyl 3,4-dimethyl-4-pentenoate.

Workup

  1. customIn a 3 l flask equipped with a mechanical stirrer and a condenser
  2. temperaturewas heated at 118° for 72 h in order
  3. customto distil the ethanol gradually as it
  4. customwas formed
  5. customThe excess of triethylorthoacetate was recovered
  6. distillationthe distillation
  7. customThe raw product thus obtained (69.0 g)
  8. customPurification on a Fischer column

Sources & evidence

ORD record
ord-26b3d30548f34e8c823a8217bb606e97
Source dataset
uspto-grants-1992_11
Patent number
US05162588

Reaction notes

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