Einecs 211-027-4 → 2,6-Dimethyl-4-(3-methyl-1H-indol-2-yl)phenol

HRID 2309404Notes

Reaction equation

HRID 2309404 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH3:19])=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:5][C:4]=1[CH3:20].[Cl-].[NH+]1C=CC=CC=1>O>[OH:2][C:3]1[C:4]([CH3:20])=[CH:5][C:6]([C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH3:19])=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 69401Einecs 211-027-4HCID 136701412-(4-Methoxy-3,5-dimethylphenyl)-3-methylindole

Product 1

HCID 136701422,6-Dimethyl-4-(3-methyl-1H-indol-2-yl)phenolYield 63.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.3 g of 2-(4-methoxy-3,5-dimethylphenyl)-3-methylindole and 13 g of pyridinium chloride were reacted at 200° C. for 1.5 hours. The reaction mixture was cooled, poured into water, extracted with ethyl acetate, washed with water, and dried. The solvent was evaporated, and the residue was recrystallized from benzene-hexane to give 2.6 g of 2-(4-hydroxy-3,5-dimethylphenyl)-3-methylindole.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. customThe solvent was evaporated
  6. customthe residue was recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-b3a29044874c44b495ff169bdfa34147
Source dataset
uspto-grants-1987_09
Patent number
US04695581

Reaction notes

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