1,4-Dioxaspiro[4.5]dec-7-ene-8-methanol, 7,9,9-trimethyl- → 7,9,9-Trimethyl-1,4-dioxaspiro[4.5]dec-7-ene-8-carbaldehyde

HRID 1283179Notes

Reaction equation

HRID 1283179 reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2([CH2:9][C:10]([CH3:15])([CH3:14])[C:11]=1[CH2:12][OH:13])[O:8][CH2:7][CH2:6][O:5]2>[O-2].[O-2].[Mn+4].C(Cl)Cl>[CH3:1][C:2]1[CH2:3][C:4]2([CH2:9][C:10]([CH3:15])([CH3:14])[C:11]=1[CH:12]=[O:13])[O:5][CH2:6][CH2:7][O:8]2

Participants

4

Reactant 1

HCID 109548611,4-Dioxaspiro[4.5]dec-7-ene-8-methanol, 7,9,9-trimethyl-

Product 1

HCID 142400447,9,9-Trimethyl-1,4-dioxaspiro[4.5]dec-7-ene-8-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

3 kg. of manganese dioxide was added in 4 portions over a period of 2 days to a solution of 150 g. of crystalline 7,9,9-trimethyl-1,4-dioxaspiro [4,5] dec-7-en-8-methanol in 3 l. of methylene chloride. After the mixture was stirred under nitrogen for an additional day, the oxidation was complete according to a determination by thin layer chromatagraphy. Filtration and evaporation of the solvent yielded the crude product which was used for the next step without further purification. A small portion of this product was purified by vacuum distillation. This product was identified as 7,9,9-trimethyl-1,4-dioxaspiro [4,5] dec-7-en-8-carboxaldehyde.

Workup

  1. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-54d3a5a574ee4889a16aec7d08c22d1e
Source dataset
uspto-grants-1976_08
Patent number
US03974181

Reaction notes

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