Hydrochloric Acid → 2,3,4-Trichlorobenzoic acid
Reaction equation
[OH-:1].[Na+].BrBr.[Cl:5][C:6]1[C:11]([Cl:12])=[C:10]([Cl:13])[CH:9]=[CH:8][C:7]=1[C:14](=[O:16])C.Cl>O.O1CCOCC1>[Cl:5][C:6]1[C:11]([Cl:12])=[C:10]([Cl:13])[CH:9]=[CH:8][C:7]=1[C:14]([OH:16])=[O:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Sodium hydroxide (45.42 g, 1.090 mol) was dissolved in water (220 ml), and while cooling with ice, bromine (16.85 ml, 0.327 mol) was dripped therein over a period of 5 minutes. After stirring the reaction solution at 0° C. for 15 minutes, a dioxane (220 ml) solution of 2′,3′,4′-trichloroacetophenone (24.40 g, 0.109 mol) was dripped therein at 0° C. over a period of 30 minutes. After stirring at room temperature for 14 hours, water (350 ml) was added and then washed with dichloromethane (350 ml). The aqueous layer obtained was gradually made acidic with concentrated hydrochloric acid while cooling with ice and the resulting crystals were filtered out. After washing the filtered-out crystals with water, the water was removed by azeotropic distillation with toluene. 22.33 g (91%) of the title compound was thereby obtained as a pale yellow powder.
Workup
- waitat 0° C. over a period of 30 minutes
- stirringAfter stirring at room temperature for 14 hours
- washwashed with dichloromethane (350 ml)
- customThe aqueous layer obtained
- temperaturewhile cooling with ice
- filtrationthe resulting crystals were filtered out
- washAfter washing the filtered-out crystals with water
- customthe water was removed by azeotropic distillation with toluene
Sources & evidence
- ORD record
- ord-0be4269d960a485596c94d5be8ef7711
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902226B2
Reaction notes
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