Ethanol → Ethyl 2-methyl-4-pentenoate

HRID 1288359Notes

Reaction equation

HRID 1288359 reaction equation
[C:1](=O)(O)[O-].[Na+].P(=O)(O)(O)O.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:12][CH3:13].[CH2:18](O)[CH3:19]>>[CH2:16]([O:15][C:11](=[O:14])[CH:12]([CH3:1])[CH2:13][CH:18]=[CH2:19])[CH3:17]

Participants

5

Reactant 4

HCID 702EthanolHCID 1004Phosphoric AcidHCID 7749Ethyl PropionateHCID 516892Sodium Bicarbonate

Product 1

HCID 62024Ethyl 2-methyl-4-pentenoate

Procedure

The autoclave is then opened and 12.6 g sodium bicarbonate is added to the reaction mass in order to neutralize the phosphoric acid. 30 g Primol (a registered trademark for mineral oil manufactured by the Exxon Co. of Linden, N.J.) is then added as a still base, and the reaction mass is fractionally distilled on a 1 inch × 20 inch packed Goodloe distillation column (i) at atmospheric pressure and 129° C (yielding a mixture of ethanol and ethyl propionate (245 g) and (ii) at 40 mm Hg. pressure and 75° C (yielding 264 g of ethyl-2-methyl-4-pentenoate. Yield, based on triethyl orthopropionate used, 73.5%.

Workup

  1. addition) is then added as a still base, and the reaction mass
  2. distillationis fractionally distilled on a 1 inch × 20 inch
  3. distillationGoodloe distillation column (i) at atmospheric pressure and 129° C (
  4. customyielding

Sources & evidence

ORD record
ord-aaa927763b5d404fa2e361e14e6160e1
Source dataset
uspto-grants-1976_10
Patent number
US03987803

Reaction notes

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