Water → 4-(3,5-Dichloro-6-fluoro-2-pyridyloxy)-2-buten-1-ol

HRID 1448409

Reaction equation

HRID 1448409 reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[N:4][C:5](F)=[C:6]([Cl:8])[CH:7]=1.[OH-:11].[Na+].[OH2:13]>C(O)CO>[Cl:8][C:6]1[C:5]([O:11][CH2:3][CH:2]=[CH:7][CH2:6][OH:13])=[N:4][C:3]([F:10])=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 6432773,5-Dichloro-2,6-difluoropyridine

Product 1

HCID 536554974-(3,5-Dichloro-6-fluoro-2-pyridyloxy)-2-buten-1-ol

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a solution of 11 grams (0.06 mole) of 3,5-dichloro-2,6-difluoropyridine in 35 milliliters of ethylene glycol was added over a 15 minute period 2.44 grams of sodium hydroxide in 35 milliliters of butenediol(2-butene-1,4-diol). The mixture was heated to ~70° C. and agitated for ~31/2 hours. Thereafter the mixture was poured into water and extracted with hot hexane. Most of the hexane was removed and upon cooling the 4-(3,5-dichloro-6-fluoro-2-pyridyloxy)-2-buten-1-ol product precipitated out. The product was recovered in a yield of 9 grams (60 percent of theoretical) and melted at 30° C. Upon analysis, the product was found to have carbon, hydrogen, chlorine and nitrogen contents of 43.3, 2.8, 27.8 and 5.6 percent, respectively, as compared with the theoretical contents of 42.9, 3.2, 28.1 and 5.6 percent, respectively, as calculated for the above named structure.

Workup

  1. temperatureThe mixture was heated to ~70° C.
  2. extractionextracted with hot hexane
  3. customMost of the hexane was removed
  4. temperatureupon cooling the 4-(3,5-dichloro-6-fluoro-2-pyridyloxy)-2-buten-1-ol product
  5. customprecipitated out
  6. customThe product was recovered in a yield of 9 grams (60 percent of theoretical) and melted at 30° C

Sources & evidence

ORD record
ord-3a3da65924804d2eadbc59d275403fa2
Source dataset
uspto-grants-1979_12
Patent number
US04180395

Linked notes

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