Reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[N:4][C:5](F)=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+].O.[CH2:14]([OH:17])[CH2:15][OH:16]>>[Cl:8][C:6]1[C:5]([O:16][CH2:15][CH2:14][OH:17])=[N:4][C:3]([F:10])=[C:2]([Cl:1])[CH:7]=1Participants
Procedure
To a solution of 12 grams (0.065 mole) of 3,5-dichloro-2,6-difluoropyridine in 35 milliliters of ethylene glycol was added over a 10 minute period 2.7 grams of anhydrous sodium hydroxide in 40 milliliters of ethylene glycol. The reaction mixture was maintained at ~70° C. with agitation for 10 minutes, cooled and poured into water. The insoluble material is removed by filtration and the filtrate extracted with methylene chloride and dried. The solid 2-(3,5-dichloro-6-fluoro-2-pyridyloxy) ethanol product was crystallized from hexane and recovered in a yield of 9 grams (61 percent of theoretical). The product melted at 65°-67° C. and was found by analysis to have carbon, hydrogen, chlorine and nitrogen contents of 37.4, 3.1, 31.5 and 6.4 percent, respectively, as compared with the theoretical contents of 37.2, 2.7, 31.4 and 6.2 percent, respectively, calculated for the above-named compound.
Workup
- temperatureThe reaction mixture was maintained at ~70° C. with agitation for 10 minutes
- temperaturecooled
- customThe insoluble material is removed by filtration
- extractionthe filtrate extracted with methylene chloride
- customdried
- customThe solid 2-(3,5-dichloro-6-fluoro-2-pyridyloxy) ethanol product was crystallized from hexane
- customrecovered in a yield of 9 grams (61 percent of theoretical)
Sources & evidence
- ORD record
- ord-5789e819244d4b7b9bd9c07fed8cc13b
- Source dataset
- uspto-grants-1979_12
- Patent number
- US04180395
Linked notes
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