Furfuryl Alcohol → Pyroxyfur

HRID 614080

Reaction equation

HRID 614080 reaction equation
[OH-].[Na+].[OH:3][CH2:4][C:5]1[O:6][CH:7]=[CH:8][CH:9]=1.[Cl:10][C:11]1[CH:16]=[C:15]([C:17]([Cl:20])([Cl:19])[Cl:18])[CH:14]=[C:13](Cl)[N:12]=1>O>[Cl:10][C:11]1[CH:16]=[C:15]([C:17]([Cl:18])([Cl:19])[Cl:20])[CH:14]=[C:13]([O:3][CH2:4][C:5]2[O:6][CH:7]=[CH:8][CH:9]=2)[N:12]=1

Participants

5

Reactant 3

HCID 7361Furfuryl AlcoholHCID 14798Sodium HydroxideHCID 897822,6-Dichloro-4-(trichloromethyl)pyridine

Product 1

HCID 129813PyroxyfurYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

To 24 grams (0.6 mole) of sodium hydroxide dissolved in 120 mls of water, was added 300 mls of 2-(hydroxymethyl)furan and the solution warmed to 50° C. In this mixture was added incremently over a 20 minute period, 106.15 grams (0.4 mole) of 2,6-dichloro-4-(trichloromethyl)pyridine. The mixture was heated to ~80° C. for ~3.5 hours and thereafter diluted with water and extracted with hexane. The extract was washed with water and the hexane evaporated off leaving ~114 grams (~87 percent of theoretical) 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 and nitrogen contents of 40.41, 2.21 and 4.21 percent, respectively, as compared with the theoretical contents of 40.40, 2.16 and 4.28 percent, respectively, as calculated for the above named compound.

Workup

  1. additionIn this mixture was added incremently over a 20 minute period
  2. temperatureThe mixture was heated to ~80° C. for ~3.5 hours
  3. extractionextracted with hexane
  4. washThe extract was washed with water
  5. customthe hexane evaporated off

Sources & evidence

ORD record
ord-465154c22d344e468baac5ba686cee15
Source dataset
uspto-grants-1979_03
Patent number
US04143144

Linked notes

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