2,2,3,6-Tetramethylcyclohexanone → 1,2,2,4-Tetramethyl-3-methylene-cyclohexane

HRID 1090491Notes

Reaction equation

HRID 1090491 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:9]([CH3:10])[CH2:8][CH2:7][CH:6]([CH3:11])[C:3]21O[CH2:4]2.CC1(C)C(C)CCC(C)C1C=O.CC1(C)C(C)CCC(C)C1=O>>[CH3:10][CH:9]1[CH2:8][CH2:7][CH:6]([CH3:11])[C:3](=[CH2:4])[C:2]1([CH3:12])[CH3:1]

Participants

4

Reactant 3

HCID 51304442,2,3,6-TetramethylcyclohexanoneHCID 187910572,2,3,6-TetramethylcyclohexanecarbaldehydeHCID 187910594,4,5,8-Tetramethyl-1-oxaspiro[2.5]octane

Product 1

HCID 199154391,2,2,4-Tetramethyl-3-methylene-cyclohexane

Procedure

The present invention provides a process for the preparation of 4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane which compound can then be converted into useful 2,2,3,6-tetramethyl-cyclohexane-carbaldehyde by treating it with a Lewis type acid. The aldehyde thus obtained possesses a high degree of isomeric purity (equal or higher than 90%). The process of the invention consists in the methylenation of 2,2,3,6-tetramethyl-1-cyclohexanone to give 1,2,2,4-tetramethyl-3-methylene-cyclohexane followed by the epoxidation of the obtained compound to give 4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane.

Workup

  1. customThe present invention provides a process
  2. additionby treating it with a Lewis type acid

Sources & evidence

ORD record
ord-b79102e9b63c4128ad927f2b0daf1c05
Source dataset
uspto-grants-1992_01
Patent number
US05081312

Reaction notes

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