Sulfuric Acid → Propanoic acid, 2-((3-(4-chlorophenyl)-1,2-dimethyl-1H-indol-5-yl)oxy)-2-methyl-

HRID 66919Notes

Reaction equation

HRID 66919 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])[CH:15]=3)[N:10]([CH3:23])[C:9]=2[CH3:24])=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:26]>C(O)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18]([CH3:21])([CH3:22])[C:19]([OH:26])=[O:20])[CH:15]=3)[N:10]([CH3:23])[C:9]=2[CH3:24])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 205291772-[3-(4-chloro-phenyl)-1,2-dimethyl-1H-indole-5-yloxy]-2-methylpropanol

Product 1

HCID 3059432Propanoic acid, 2-((3-(4-chlorophenyl)-1,2-dimethyl-1H-indol-5-yl)oxy)-2-methyl-

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 6.0 g (60 m mole) of chromium trioxide in 50 ml of glacial acetic acid and 5 ml of water was added dropwise to a mixture of 19.0 g (55 m mole) of 2-[3-(4-chloro-phenyl)-1,2-dimethyl-1H-indole-5-yloxy]-2-methylpropanol, 50 ml of glacial acetic acid, 10 ml of water, and 5 ml of conc. sulfuric acid under stirring. After standing overnight, the reaction mixture was warmed for one hour on a steam bath. Subsequently the mixture was extracted with chloroform. The chloroform extracts were dried, and the evaporation residue was chromatographed on silicagel with chloroform/methanol (8:2) as eluant.

Workup

  1. temperaturethe reaction mixture was warmed for one hour on a steam bath
  2. extractionSubsequently the mixture was extracted with chloroform
  3. dry with materialThe chloroform extracts were dried
  4. customthe evaporation residue was chromatographed on silicagel with chloroform/methanol (8:2) as eluant

Sources & evidence

ORD record
ord-98c32d92967f477bb4d6e093ad134c35
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Reaction notes

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