Ethyl 6-hydroxy-4-methylhexa-2,4-dienoate → HCID 54046952, compound

HRID 1719108Notes

Reaction equation

HRID 1719108 reaction equation
[OH:1][CH2:2][CH:3]=[C:4]([CH3:12])[CH:5]=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]>ClCCl.[O-2].[Mn+4].[O-2]>[CH:2]([CH:3]=[C:4]([CH3:12])[CH:5]=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:1]

Participants

4

Reactant 1

HCID 54238884Ethyl 6-hydroxy-4-methylhexa-2,4-dienoate

Product 1

HCID 54046952HCID 54046952, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

11.7 g of ethyl 6-hydroxy-4-methyl-2,4-hexadienoate in 200 ml of dichloromethane were stirred at room temperature for 4 hours with 30 g of manganese (IV) oxide. The solution was filtered and concentrated and the residue was then recrystallized from hexane/cyclohexane. There were obtained 9.1 g (78%) of ethyl 5-formyl-4-methyl-2,4-pentadienoate of melting point 48°-49° C.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated
  3. customthe residue was then recrystallized from hexane/cyclohexane

Sources & evidence

ORD record
ord-14ed18fc516641fbbdd144af3f056f0f
Source dataset
uspto-grants-1985_09
Patent number
US04539154

Reaction notes

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