Hydrochloric Acid → Dicamba

HRID 971920

Reaction equation

HRID 971920 reaction equation
[OH:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([Cl:12])[C:3]=1[C:4]([OH:6])=[O:5].[OH-].[K+].S(OC)(O[CH3:19])(=O)=O.Cl>O>[CH3:19][O:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([Cl:12])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 14797Potassium Hydroxide2×HCID 188443,6-Dichlorosalicylic acid

Product 1

HCID 3030Dicamba

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

2-Hydroxy-3,6-dichlorobenzoic acid (44.4 g) is dissolved in a solution of potassium hydroxide (11.2 g, 0.2 mole) and water (100 ml). The solution is heated to reflux (about 100° C.) and stirred vigorously while dimethyl sulfate (63.1 g, 0.5 mole) is added dropwise. The reaction mixture is then treated with a solution of potassium hydroxide (14.0 g, 0.25 mole) in 25.0 ml of water and refluxed for an additional 2 hours. The reaction mixture is then cooled and acidified to Congo red with hydrochloric acid to precipitate the desired 2-methoxy-3,6-dichlorobenzoic acid.

Workup

  1. temperatureThe solution is heated
  2. additionis added dropwise
  3. temperaturerefluxed for an additional 2 hours
  4. temperatureThe reaction mixture is then cooled
  5. customto precipitate the desired 2-methoxy-3,6-dichlorobenzoic acid

Sources & evidence

ORD record
ord-c60020878259412b8573d192325b9d4d
Source dataset
uspto-grants-1979_07
Patent number
US04161611

Linked notes

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