HCID 67838128, compound → 2,2,3,6-Tetramethylcyclohex-3-ene-1-carbaldehyde

HRID 892670Notes

Reaction equation

HRID 892670 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[CH3:12][C:13]1([CH3:23])[C:18]([CH3:19])=[CH:17][CH2:16][C@H:15]([CH3:20])[C@@H:14]1[CH2:21][OH:22]>C(Cl)Cl>[CH3:23][C:13]1([CH3:12])[C:18]([CH3:19])=[CH:17][CH2:16][CH:15]([CH3:20])[CH:14]1[CH:21]=[O:22]

Participants

4

Reactant 2

HCID 67838128HCID 67838128, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 198960782,2,3,6-Tetramethylcyclohex-3-ene-1-carbaldehydeYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Prepared according to the method described, starting from 15.0 g (70 mmol) of PCC in 150 ml of CH2Cl2 and 8.38 g (50 mmol) of cis-2,2,3,6-tetramethyl-3-cyclohexene-1-methanol, obtained as in example 3b., in 50 ml of CH2Cl2. After stirring for 1 h, the reaction mixture was treated as described above to yield 6.77 g of the desired aldehyde in the form of a yellow oil (2 isomers, cis/trans~9:1).

Workup

  1. customPrepared
  2. customobtained as in example 3b
  3. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-7ba4cea5b60a4a8695a6daee5abe54ca
Source dataset
uspto-grants-1992_06
Patent number
US05118865

Reaction notes

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