HCID 86733812, compound → HCID 86733811, compound

HRID 1283180Notes

Reaction equation

HRID 1283180 reaction equation
[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([CH2:4][C:5]([CH3:20])=[C:6]([CH:13]=[CH:14][C:15]([CH3:19])=[CH:16][CH2:17][OH:18])[C:7]2([CH3:12])[CH3:11])[O:2]1>[O-2].[O-2].[Mn+4].C1C=CC=CC=1>[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([CH2:4][C:5]([CH3:20])=[C:6]([CH:13]=[CH:14][C:15]([CH3:19])=[CH:16][CH:17]=[O:18])[C:7]2([CH3:11])[CH3:12])[O:2]1

Participants

4

Reactant 1

HCID 86733812HCID 86733812, compound

Product 1

HCID 86733811HCID 86733811, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

500 g. of manganese dioxide was added in 3 portions over 9 hours to a solution of 42 g. of crude 5-(4-ethylenedioxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienol in 1 l. of benzene. During this period a suspension formed. The suspension was then stirred under nitrogen for 24 hours. Filtration and evaporation of the solvent yielded a light yellow oil which was used for the next steps without further purification. The yellow oil was purified by chromatography on silica gel G. The yellow oil was identified as 5-(4-Ethylenedioxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienal.

Workup

  1. customDuring this period a suspension formed
  2. filtrationFiltration and evaporation of the solvent
  3. customyielded a light yellow oil which
  4. customwas used for the next steps without further purification
  5. customThe yellow oil was purified by chromatography on silica gel G

Sources & evidence

ORD record
ord-33fc37daa8ad404b90e28bb9a8d8a3f9
Source dataset
uspto-grants-1976_08
Patent number
US03974181

Reaction notes

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