Propionic Acid → Ethyl 2-methyl-3,4-pentadienoate

HRID 1834343Notes

Reaction equation

HRID 1834343 reaction equation
C(=O)(O)[O-].[Na+].[C:6](O)(=[O:9])[CH2:7]C.C[C:12]1[CH:17]=[C:16]([C:18](C)(C)C)[C:15]([OH:22])=C(C(C)(C)C)[CH:13]=1>>[CH2:6]([O:9][C:15](=[O:22])[CH:16]([CH3:18])[CH:17]=[C:12]=[CH2:13])[CH3:7]

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 516892Sodium Bicarbonate

Product 1

HCID 62166Ethyl 2-methyl-3,4-pentadienoate

Conditions

Temperature
150 °C

Procedure

The autoclave is closed and the reaction mass is heated to 150° C. over a period of 50 minutes. The reaction mass is then maintained at a temperature of between 135°-160° C and at a pressure of 20 up to 60 psig for a period of 3 hours. At the end of this 3-hour period, the autoclave is opened and the reaction mass is cooled to room temperature. 12.6 g of sodium bicarbonate is then added to the reaction mass in order to neutralize the propionic acid. 30 g of Primol ® (see note 1) and 0.1 g of Ionol ® (see note 2) are added and the resulting reaction product is fractionally distilled at atmospheric pressure to a pot temperature of 129° C. A mixture of ethanol and ethyl propionate is distilled over. Vacuum is then applied to the distillation column and the resultant product, ethyl-2-methyl-3,4-pentadienoate is distilled at a vapor temperature of 65°-69° C at a pressure of 24-33 mm Hg as fractions 5-10 of the following fractions:

Workup

  1. customThe autoclave is closed
  2. temperatureThe reaction mass is then maintained at a temperature of between 135°-160° C and at a pressure of 20 up to 60 psig for a period of 3 hours
  3. customAt the end of this 3-hour period
  4. temperaturethe reaction mass is cooled to room temperature
  5. customthe resulting reaction product
  6. distillationis fractionally distilled at atmospheric pressure to a pot temperature of 129° C
  7. additionA mixture of ethanol and ethyl propionate
  8. distillationis distilled over
  9. distillationVacuum is then applied to the distillation column
  10. distillationthe resultant product, ethyl-2-methyl-3,4-pentadienoate is distilled at a vapor temperature of 65°-69° C at a pressure of 24-33 mm Hg as fractions 5-10 of the following fractions

Sources & evidence

ORD record
ord-2969864792f24918b769864e3645f8cb
Source dataset
uspto-grants-1978_01
Patent number
US04069828

Reaction notes

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