Sodium Hydroxide → 1-Phenylindole-3-acetic acid

HRID 863546Notes

Reaction equation

HRID 863546 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][C:17]([O:19]CC)=[O:18])=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][C:17]([OH:19])=[O:18])=[CH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53656737Ethyl 1-phenylindole-3-acetate

Product 1

HCID 196961141-Phenylindole-3-acetic acidYield 98.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.3 g (22.6 mmol) of ethyl 1-phenylindole-3-acetate in 20 ml of ethanol was treated with 20 ml (40 mmol) of 2M sodium hydroxide solution and left at room temperature for 17 hours. Ethanol was removed under reduced pressure and the aqueous solution was washed with two 20 ml portions of diethyl ether. The aqueous phase was acidified with concentrated hydrochloric acid and the suspension obtained was stored at 0° C. for 2 hours. The suspension was filtered and the solid was crystallized from methanol/water (2:1) to give 5.6 g 1-phenylindole-3-acetic acid as a blue-grey solid of melting point 131°-135° C.

Workup

  1. customEthanol was removed under reduced pressure
  2. washthe aqueous solution was washed with two 20 ml portions of diethyl ether
  3. customthe suspension obtained
  4. waitwas stored at 0° C. for 2 hours
  5. filtrationThe suspension was filtered
  6. customthe solid was crystallized from methanol/water (2:1)

Sources & evidence

ORD record
ord-526418cf1e1d45c1b56d422a78e3b759
Source dataset
uspto-grants-1998_02
Patent number
US05721230

Reaction notes

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