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 267315Notes

Reaction equation

HRID 267315 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>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

3

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 1

HCID 6344DichloromethaneSolvent

Procedure

3 kg. of maganese dioxide was added in four 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 chromatography. 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-40039ac44ecd4c10b2f5bea7cef452e4
Source dataset
uspto-grants-1976_03
Patent number
US03941841

Reaction notes

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