Acetic Acid → 2,4-Pentadienoic acid, methyl ester

HRID 371187Notes

Reaction equation

HRID 371187 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH:2]=[CH:3][CH:4]=[CH2:5].O=O.[C:11]([OH:14])(=[O:13])[CH3:12]>>[C:1]([O:7][CH3:8])(=[O:6])[CH:2]=[CH:3][CH:4]=[CH2:5].[C:11]([O:14][CH:3]([CH:4]=[CH:5][CH2:8][O:7][C:1](=[O:6])[CH3:2])[CH2:2][C:1]([O:7][CH3:8])=[O:6])(=[O:13])[CH3:12].[C:11]([O:14][CH:5]=[CH:4][CH:3]=[CH:2][C:1]([O:7][CH3:8])=[O:6])(=[O:13])[CH3:12]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 977OxygenHCID 736882,4-Pentadienoic acid, methyl ester

Product 3

HCID 736882,4-Pentadienoic acid, methyl esterHCID 53778357HCID 53778357, compoundHCID 54019472HCID 54019472, compound

Procedure

56 g of methyl 2,4-pentadienoate are suspended in 543 g of glacial acetic acid in the presence of 50 g of a Pd/Cu catalyst (5% of Pd and 9.2% of Cu) prepared as described in German Laid-Open Application DOS No. 2,820,519, and reacted with 12 liters of oxygen at 95° C. in the course of 4 hours, all as described in Example 1. The mixture is worked up as described in Example 1 and then fractionally distilled, giving, in addition to unreacted methyl 2,4-pentadienoate, 13 g of methyl 2,5-diacetoxypent-3-enecarboxylate of boiling point 113°-115° C./0.4 mbar (nD20 =1.4600) and 19.5 g of methyl 5-acetoxy-2,4-pentadienoate of boiling point 125°-131° C./13 mbar and melting point 54°-56° C. (from methanol).

Workup

  1. customprepared
  2. distillationfractionally distilled

Sources & evidence

ORD record
ord-4e51931a4c1b474d9d0b25fe9ac382f5
Source dataset
uspto-grants-1985_07
Patent number
US04529814

Reaction notes

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