Pyridine → HCID 86739258, compound

HRID 1388645Notes

Reaction equation

HRID 1388645 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]([CH3:21])(/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:9][OH:10].C([O-])(O)=O.[Na+]>ClCCl.[O-2].[O-2].[O-2].[Cr+6]>[CH3:7][C:8]([CH3:21])(/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:9]=[O:10]

Participants

6

Reactant 3

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 86739259HCID 86739259, compound

Product 1

HCID 86739258HCID 86739258, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution of 2.25 g (27 mmoles) of pyridine in 30 ml of dichloromethane was added 1.38 g (13.8 mmoles) of chromium trioxide in portions. A solution of 0.345 g (1.65 mmoles) of (Z,Z)-2,2-dimethyl-3,6-dodecadien-1-ol in 5 ml of dichloromethane was slowly added to the stirred suspension at room temperature. After stirring at room temperature for 12 hours, the mixture was poured into 10% aqueous NaHCO3 solution and the product was extracted with ether. The ether extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silica gel. Elution with 9:1 hexane-ether afforded 0.195 g (57%) of (Z,Z)-2,2-dimethyl-3,6-dodecadienal.

Workup

  1. extractionthe product was extracted with ether
  2. extractionThe ether extract
  3. washwas washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel
  7. washElution with 9:1 hexane-ether

Sources & evidence

ORD record
ord-4934603036504848996e948d8393bdb2
Source dataset
uspto-grants-1984_02
Patent number
US04432906

Reaction notes

Loading…