Pyridine → 2-​Dodecenal

HRID 462390Notes

Reaction equation

HRID 462390 reaction equation
N1C=CC=CC=1.[CH3:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][OH:19]>C(Cl)Cl.CCOCC.[O-2].[O-2].[O-2].[Cr+6]>[CH:18](=[O:19])/[CH:17]=[CH:16]\[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH3:7]

Participants

6

Reactant 2

HCID 1049PyridineHCID 53646263-Dodecen-1-ol, (3Z)-

Product 1

HCID 53548992-​DodecenalYield 94.8%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9.5 ml of pyridine in 150 ml of methylene chloride was treated in one portion with 6.0 g of chromium trioxide. The mixture was stirred for 15 minutes at room temperature and then 1.60 g of 3Z-dodecen-1-ol in 3 ml of methylene chloride was added. After 5 minutes the reaction mixture was diluted with 200 ml of ether and then filtered through celite. The filtrate was washed three times with 100 ml of 5% aqueous sodium hydroxide, then with ice-cold 5% hydrochloric acid, saturated sodium bicarbonate and finally with brine. After drying over sodium sulfate, the solvent was evaporated giving 1.5 g of 3Z-dodecen-1-al.

Workup

  1. filtrationfiltered through celite
  2. washThe filtrate was washed three times with 100 ml of 5% aqueous sodium hydroxide
  3. dry with materialAfter drying over sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-36362d9b7e3b47148ac70e51a150ca28
Source dataset
uspto-grants-1985_05
Patent number
US04515727

Reaction notes

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