2-Octanol → Fluroxypyr-meptyl

HRID 249421Notes

Reaction equation

HRID 249421 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[N:5]=[C:4]([O:10][CH2:11][C:12](OC)=[O:13])[C:3]=1[Cl:16].[CH3:17][CH:18]([OH:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[N:5]=[C:4]([O:10][CH2:11][C:12]([O:25][CH:18]([CH3:17])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:13])[C:3]=1[Cl:16]

Participants

3

Reactant 2

HCID 200832-OctanolHCID 5463802Methyl 2-(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxyacetate

Product 1

HCID 54745Fluroxypyr-meptyl

Conditions

Temperature
130 °C

Procedure

Methyl (4-amino-3,5-dichloro-6-fluoro-2--pyridinyloxy)acetate (1375 g of 98.0 percent assay, 5.02 moles) was combined with 1901 g (14.6 moles of 1-methylheptanol (2-octanol) in a 5 liter flask equipped with a stirrer, a 30 centimeter (cm) Vigreaux column and distillation head, and a thermometer. The solution was heated to about 130° C. at 10 kiloPascals (kPa) pressure to remove any water present in the system. A 1.3 g portion of tetrabutyl titanate catalyst was added and the mixture was heated at about 150° C. under 60 kPa pressure for 6 hours, distilling out the nethanol as it formed. The pressure was slowly reduced to about 3.3 kPa and the excess 1-methylheptanol was removed by distillation along with any other volatiles. The residue, which amounted to 1857 g, was the title compound. It was found to be 97.4 percent pure and to contain 0.2 percent unreacted methyl ester and 0.1 percent 1-methylheptanol. The yield was, accordingly, 98 7 percent of theory.

Workup

  1. customequipped with a stirrer
  2. distillationa 30 centimeter (cm) Vigreaux column and distillation head
  3. customto remove any water present in the system
  4. additionA 1.3 g portion of tetrabutyl titanate catalyst was added
  5. temperaturethe mixture was heated at about 150° C. under 60 kPa pressure for 6 hours
  6. distillationdistilling out the nethanol as it
  7. customformed
  8. customthe excess 1-methylheptanol was removed by distillation along with any other volatiles

Sources & evidence

ORD record
ord-00a08238040549e79aff767928286ad9
Source dataset
uspto-grants-1993_05
Patent number
US05214150

Reaction notes

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