Water → 129410-14-6

HRID 1166732Notes

Reaction equation

HRID 1166732 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[CH2:12][C:13]([O:15]CC)=[O:14])=[O:2].[OH-].[Na+].O>O1CCOCC1>[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[CH2:12][C:13]([OH:15])=[O:14])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14636514HCID 14636514, compound

Product 1

HCID 14636516129410-14-6Yield 73.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl (3-formylindolyl)acetate (15.9 g) was dissolved in 1,4-dioxane (100 ml) and added 36% aq. NaOH (10 ml). The resulting mixture was stirred at room temperature for 4 days. Water (500 ml) was added and the mixture was washed with diethyl ether (150 ml). The aqueous phase was made acidic with 5N HCl and extracted with ethyl acetate (250+150 ml). The combined organic extracts were dried (MgSO4) and evaporated in vacuo to afford 10.3 g (73% over two steps) of (3-formylindolyl)acetic acid.

Workup

  1. washthe mixture was washed with diethyl ether (150 ml)
  2. extractionextracted with ethyl acetate (250+150 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-638396717df744eca963f6a05ccc1ef3
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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