Ethanol → Ethyl 1H-indole-3-acetate

HRID 344716Notes

Reaction equation

HRID 344716 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([OH:13])=[O:12])=[CH:2]1.S(=O)(=O)(O)O.[OH-].[Na+].[CH2:21](O)[CH3:22]>>[CH2:21]([O:12][C:11]([CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:13])[CH3:22]

Participants

5

Reactant 4

HCID 702EthanolHCID 802Indole-3-Acetic AcidHCID 1118Sulfuric AcidHCID 14798Sodium Hydroxide

Product 1

HCID 13067Ethyl 1H-indole-3-acetateYield 90%

Conditions

Temperature
0 °C

Procedure

A mixture of 5.0 g (28.5 mmols) of indole-3acetic acid, 250 ml of ethanol and 5 ml of conc. sulfuric acid was heated under reflux for 2 hours. After cooling to 0° C., the mixture was neutralized with a 2 normal aqueous sodium hydroxide solution. The solvent was evaporated under reduced pressure, and then water was added to the residue followed by extraction of the solution with chloroform. The chloroform layer was washed with an aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was dried to afford 5.2 g (yield: 90%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was evaporated under reduced pressure
  4. additionwater was added to the residue
  5. extractionfollowed by extraction of the solution with chloroform
  6. washThe chloroform layer was washed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was dried

Sources & evidence

ORD record
ord-1713a83d80b14f36bfc94b17e470b70f
Source dataset
uspto-grants-1991_10
Patent number
US05053408

Reaction notes

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