Potassium Hydroxide → HCID 21389583, compound

HRID 1833548Notes

Reaction equation

HRID 1833548 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH3:15])=[CH:7]1)C.[OH-].[K+]>CO.CO.O>[CH3:15][C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]([CH2:5][C:4]([OH:16])=[O:3])[CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 43316681HCID 43316681, compound

Product 1

HCID 21389583HCID 21389583, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

The residue, 3-methyl-indole-1-acetic acid ethyl ester, is dissolved in 900 ml of methanol, potassium hydroxide (90 g) in 400 ml of 1:1 methanol-H2O is then added. The mixture is stirred at room temperature for 11/2 hours. The methanol is evaporated under reduced pressure. The residue is diluted with water (800 ml) and extracted (3x) with ether. Acidification with 6NHCl of the aqueous phase yields 3-methyl-indole-1-acetic acid, m.p. 174°-176° C.

Workup

  1. customThe methanol is evaporated under reduced pressure
  2. additionThe residue is diluted with water (800 ml)
  3. extractionextracted (3x) with ether

Sources & evidence

ORD record
ord-cbd22d29208d4b7c99d9022f23a6f7d5
Source dataset
uspto-grants-1978_01
Patent number
US04066763

Reaction notes

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