Hydrochloric Acid → Cloquintocet

HRID 716674Notes

Reaction equation

HRID 716674 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([O:16]C(C)CCCCC)=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Cl>O>[CH:5]1[CH:6]=[N:7][C:8]2[C:3](=[C:2]([Cl:1])[CH:11]=[CH:10][C:9]=2[O:12][CH2:13][C:14]([OH:16])=[O:15])[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 93528Cloquintocet-mexyl

Product 1

HCID 15257197CloquintocetYield 71.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 70.70 g of cloquintocet-mexyl (96.9% strength) in 205 g of demineralised water was stirred at 100° C. in a 1 L jacketed glass vessel. 27.5 g of aqueous hydrochloric acid [32%] was slowly added, and the reaction mixture was stirred under reflux for 6 hours. The biphasic solution was then cooled down to 20° C. over 4 hours and the resulting suspension was filtered and the solid was wash with 2×50 mL of demineralised water and dried. Cloquintocet acid hydrochloride (35.55 g) was isolated as a light brown solid.

Workup

  1. stirringthe reaction mixture was stirred
  2. temperatureunder reflux for 6 hours
  3. temperatureThe biphasic solution was then cooled down to 20° C. over 4 hours
  4. filtrationthe resulting suspension was filtered
  5. washthe solid was wash with 2×50 mL of demineralised water
  6. customdried

Sources & evidence

ORD record
ord-b549e4efa8834453b1c170699f06d15a
Source dataset
uspto-grants-2015_11
Patent number
US09193686B2

Reaction notes

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