Potassium Hydroxide → HCID 21274215, compound
Reaction equation
[OH-].[K+].[Cl:3][C:4]1[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[C:9]2[C:5]=1[C:6]([CH2:15][C:16]([O:18]C)=[O:17])=[CH:7][NH:8]2>O.CO>[Cl:3][C:4]1[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[C:9]2[C:5]=1[C:6]([CH2:15][C:16]([OH:18])=[O:17])=[CH:7][NH:8]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
An aqueous solution containing 8.4 g (0.15 mole) of potassium hydroxide in 10 ml of water was added to a solution of 4.3 g (0.015 mole) of methyl 4,5,7-trichloroindole-3-acetate in 50 ml of methanol, and the resulting mixture was heated at 50° C. for 10 hours, after which the reaction mixture was concentrated under reduced pressure until it became an aqueous solution. Said aqueous solution was acidified with acetic acid and extracted with ethyl acetate. The ethyl acetate phase was washed with water and a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate, and subsequently the ethyl acetate was removed by distillation under reduced pressure to obtain crude 4,5,7-trichloroindole-3-acetic acid, which was then purified by a column chromatography (silica gel) to obtain 3.3. g of the desired compound represented by the formula: ##STR16##
Workup
- concentrationafter which the reaction mixture was concentrated under reduced pressure until it
- extractionextracted with ethyl acetate
- washThe ethyl acetate phase was washed with water
- dry with materiala saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate
- customsubsequently the ethyl acetate was removed by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-3d2ab68c3b8f40e4951ae825b918e680
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04806143
Reaction notes
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