Furfuryl Alcohol → Pyroxyfur

HRID 614081

Reaction equation

HRID 614081 reaction equation
CCCCCC.[H-].[Na+].[OH:9][CH2:10][C:11]1[O:12][CH:13]=[CH:14][CH:15]=1.[Cl:16][C:17]1[CH:22]=[C:21]([C:23]([Cl:26])([Cl:25])[Cl:24])[CH:20]=[C:19](Cl)[N:18]=1>C(COC)OC.O>[Cl:16][C:17]1[CH:22]=[C:21]([C:23]([Cl:24])([Cl:25])[Cl:26])[CH:20]=[C:19]([O:9][CH2:10][C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[N:18]=1

Participants

7

Reactant 4

HCID 7361Furfuryl AlcoholHCID 8058HexaneHCID 24758Sodium hydrideHCID 897822,6-Dichloro-4-(trichloromethyl)pyridine

Product 1

HCID 129813PyroxyfurYield 58.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent4×

Conditions

Temperature
50 °C

Procedure

To 5.5 grams (0.115 mole) of hexane washed sodium hydride in 100 mls of dimethoxyethane was added over a 25 minute period, 11.28 grams (0.115 mole) of 2-(hydroxymethyl)furan dissolved in 30 mls of dimethoxyethane. An additional 25 mls of dimethoxyethane was added and the mixture heated to 50° C. for about 10 minutes. To this mixture was added 26.54 grams (0.1 mole) of 2,6-dichloro-4-(trichloromethyl)pyridine dissolved in 100 mls of dimethoxyethane. The mixture was heated under reflux (83° C.) for about 2.5 hours and the reaction mixture added to 600 mls of water and extracted with methylene chloride. The methylene chloride was evaporated from the extract leaving a black oil. This oil was distilled under reduced pressure to obtain 19.05 grams of the desired 2-chloro-6-(2-furanylmethoxy)-4-(trichloromethyl)pyridine product. The product, an oil, had a refractive index of n 25/d = 1.5722 and upon analysis was found to have carbon, hydrogen, nitrogen and chlorine contents of 41.19, 2.50, 4.23 and 42.49 percent, respectively, as compared with the theoretical contents of 40.40, 2.16, 4.28 and 43.37 percent, respectively, as calculated for the above named compound.

Workup

  1. additionwas added over a 25 minute period
  2. temperatureThe mixture was heated
  3. temperatureunder reflux (83° C.) for about 2.5 hours
  4. extractionextracted with methylene chloride
  5. customThe methylene chloride was evaporated from the extract
  6. customleaving a black oil
  7. distillationThis oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-d4e1657eb891471ea47e22abc80d18f7
Source dataset
uspto-grants-1979_03
Patent number
US04143144

Linked notes

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