Methyl 3-pentenoate → Methyl 3-methoxyvalerate

HRID 231353Notes

Reaction equation

HRID 231353 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][CH:3]=[CH:4][CH3:5].[C:9](OC)(=[O:14])/C=C/CC.C(OC)(=O)/C=C\CC.C(OC)(=O)CCC=C>>[CH3:9][O:14][CH:3]([CH2:4][CH3:5])[CH2:2][C:1]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 4

HCID 101865Methyl 3-pentenoateHCID 543664Methyl 4-pentenoateHCID 5364718Methyl 2-pentenoateHCID 6197811methyl (Z)-pent-2-enoate

Product 1

HCID 12636344Methyl 3-methoxyvalerateYield 3%

Procedure

10 g/hour of methyl 3-methoxyvalerate were pumed into an evaporator and passed from there, in gaseous form together with 3 l of nitrogen, at 350° C., over 5 g of an SiO2 catalyst. The gaseous reaction products were condensed, weighed and analysed by gas chromatography. In the course of 6 hours, 53.3 g of the reacted mixture consisting of 30% of methyl 3-pentenoate, 56% of methyl 2-transpentenoate, 8% of methyl 2-cis-pentenoate, 2% of methyl 4-pentenoate and 3% of unconverted methyl 3-methoxyvalerate were obtained. The ratio of 3-pentenoates to 2-pentenoates was accordingly 1:2.2.

Workup

  1. custom10 g/hour of methyl 3-methoxyvalerate were pumed into an evaporator
  2. customat 350° C.
  3. customcondensed

Sources & evidence

ORD record
ord-1310fae7177348f7a98a3e456f604d39
Source dataset
uspto-grants-1989_07
Patent number
US04845269

Reaction notes

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