HCID 86736668, compound → HCID 12960829, compound

HRID 426694Notes

Reaction equation

HRID 426694 reaction equation
[F:1]/[C:2](/[C:5](/[CH3:19])=[CH:6]/[CH2:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([O:15][CH3:16])=[C:10]([CH3:17])[C:9]=1[Cl:18])=[CH:3]\[OH:4]>CCOCC.[O-2].[O-2].[Mn+4]>[F:1]/[C:2](=[C:5](/[CH3:19])\[CH:6]=[CH:7]\[C:8]1[C:13]([Cl:14])=[CH:12][C:11]([O:15][CH3:16])=[C:10]([CH3:17])[C:9]=1[Cl:18])/[CH:3]=[O:4]

Participants

4

Reactant 1

HCID 86736668HCID 86736668, compound

Product 1

HCID 12960829HCID 12960829, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 5.6 g. (18.4 mmol) of 2Z,4E-2-fluoro-3-methyl-5-(2,6-dichloro-3-methyl-4-methoxyphenyl)pentadien-1-ol in ether was added to a stirred suspension of 24 g. of activated manganese dioxide in ether. After 14 hours, thin layer chromatography indicated that all of the alcohol had reacted. The mixture was filtered through Celite. The filtrate was concentrated and the residue was chromatographed on silica gel to give 5.4 g. (95% yield) of 2Z,4E-2-fluoro-3-methyl-5-(2,6-dichloro-3-methyl-4-methoxyphenyl)pentadiene-1-al.

Workup

  1. customhad reacted
  2. filtrationThe mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated
  4. customthe residue was chromatographed on silica gel
  5. customto give 5.4 g

Sources & evidence

ORD record
ord-0e158c45fc8a4232b4ee75081a5cd00e
Source dataset
uspto-grants-1979_10
Patent number
US04171318

Reaction notes

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