Methanol → 2-Indolylacetic acid

HRID 2395265Notes

Reaction equation

HRID 2395265 reaction equation
[OH-].[Li+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[CH2:12][C:13]([O:15]C)=[O:14].CO>O.C1COCC1>[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[CH2:12][C:13]([OH:15])=[O:14]

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 10932216Methyl 2-(1H-indol-2-yl)acetate

Product 1

HCID 43717522-Indolylacetic acidYield 72.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide (346 mg, 8.25 mmol) in water (2 ml) was added to methyl indole-2-acetate (520 mg, 2.75 mmol) (prepared using the method of Capuano et al, Chem. Ber., 1986, 119, 2069) in THF (2 ml) and methanol (6 ml) and the mixture stirred for 1 h. The mixture was concentrated in vacuo, diluted with water (20 ml) and extracted with diethyl ether (2×10 ml). The aqueous layer was carefully acidified to pH 2 with 1M HCl and extracted into dichloromethane (3×20 ml). The extracts were dried (MgSO4) and evaporated in vacuo to give indole-2-acetic acid (350 mg, 72%) as a pink solid.

Workup

  1. customprepared
  2. concentrationThe mixture was concentrated in vacuo
  3. additiondiluted with water (20 ml)
  4. extractionextracted with diethyl ether (2×10 ml)
  5. extractionextracted into dichloromethane (3×20 ml)
  6. dry with materialThe extracts were dried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6467a3cca2874f298a34498c1a255505
Source dataset
uspto-grants-1998_09
Patent number
US05814644

Reaction notes

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