Thionyl Chloride → [(3,5,6-Trichloropyridin-2-yl)oxy]acetyl chloride

HRID 1089035Notes

Reaction equation

HRID 1089035 reaction equation
[Cl:1][C:2]1[C:3]([O:10][CH2:11][C:12]([OH:14])=O)=[N:4][C:5]([Cl:9])=[C:6]([Cl:8])[CH:7]=1.S(Cl)([Cl:17])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([O:10][CH2:11][C:12]([Cl:17])=[O:14])=[N:4][C:5]([Cl:9])=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 41428Triclopyr

Product 1

HCID 13491111[(3,5,6-Trichloropyridin-2-yl)oxy]acetyl chlorideYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

3,5,6-Trichloro-2-pyridyloxyacetic acid (20 g, 0.078 mole was stirred with toluene (46.5 ml). Thionyl chloride (26 ml) was added dropwise to the well-stirred mixture over 15 minutes. The mixture was then heated under reflux (70° C.) for 3 hours. The effluent gases (SO2 +HCl) were absorbed into aqueous 5N sodium hydroxide. The cooled reaction mixture was filtered and evaporated to yield the title compound (20.9 g, 98 percent) as a thick dark brown oil.

Workup

  1. temperatureThe mixture was then heated
  2. customThe effluent gases (SO2 +HCl) were absorbed into aqueous 5N sodium hydroxide
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customevaporated

Sources & evidence

ORD record
ord-b0e5fa236e20427bb8c87c7be55ca0c6
Source dataset
uspto-grants-1990_10
Patent number
US04964897

Reaction notes

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