Water → 2-(4-Hydroxy-3,5-dimethylphenyl)-5-methoxy-3-methylindole
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=O)[CH2:9][CH3:10])[CH:5]=[C:4]([CH3:12])[C:3]=1[OH:13].Cl.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23]N)=[CH:19][CH:18]=1.O>C(O)(C)C>[OH:13][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([C:8]2[NH:23][C:20]3[C:21]([C:9]=2[CH3:10])=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=3)=[CH:5][C:4]=1[CH3:12]Participants
5
Procedure
5.1 g of 2,6-dimethyl-4-propionylphenol and 5.0 g of 4-methoxyphenylhydrazine hydrochloride were dispersed in 30 ml of isopropanol, and the dispersion was refluxed for 20 hours in a nitrogen stream. Water was added to the reaction mixture, and the precipitated crystals were collected by filtration. The crystals were dissolved in ethyl acetate, and washed with a 5% aqueous sodium hydroxide solution, water, 2N hydrochloric acid and water. The organic layer was dried, and the solvent was evaporated. Recrystallization of the resulting crude crystals from ethanol-hexane gave 5.8 g of 2-(4-hydroxy-3,5-dimethylphenyl)-5-methoxy-3-methylindole.
Workup
- temperaturethe dispersion was refluxed for 20 hours in a nitrogen stream
- filtrationthe precipitated crystals were collected by filtration
- dissolutionThe crystals were dissolved in ethyl acetate
- washwashed with a 5% aqueous sodium hydroxide solution, water, 2N hydrochloric acid and water
- customThe organic layer was dried
- customthe solvent was evaporated
- customRecrystallization of the resulting crude crystals from ethanol-hexane
Sources & evidence
- ORD record
- ord-6d3afdaabe0b4af1bf50efa3a9e72f25
- Source dataset
- uspto-grants-1987_09
- Patent number
- US04695581
Reaction notes
Loading…