Hydrochloric Acid → Ethyl 1H-indole-3-acetate

HRID 1174525Notes

Reaction equation

HRID 1174525 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.Cl.[CH2:15](OCC)[CH3:16]>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH2:15][CH3:16])=[O:12])=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 802Indole-3-Acetic AcidHCID 3283Diethyl Ether

Product 1

HCID 13067Ethyl 1H-indole-3-acetateYield 158.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Indole-3-acetic acid (3.5 g, 20 mmol) was dissolved in ethanol (70 Cm3) and a solution of hydrogen chloride in diethyl ether (12 cm3, 12 mmol) was added. The reaction was heated to reflux for 5 hand upon cooling the solvent was removed under reduced pressure to provide ethyl indole-3-acetate (4 g, 19 mmol, 98%) as a yellow oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 hand
  3. temperatureupon cooling the solvent
  4. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-1d0edb2c960f4da7b5672dd373d319c1
Source dataset
uspto-grants-2010_11
Patent number
US07838518B2

Reaction notes

Loading…