Methanol → 2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine

HRID 2112233Notes

Reaction equation

HRID 2112233 reaction equation
[N+](C1C=CC(N=[N:11][C:12]2[C:13]([CH3:32])=[C:14]([CH3:31])[C:15]3[O:19][C:18]([CH3:21])([CH3:20])[CH:17]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)[C:16]=3[C:29]=2[CH3:30])=CC=1)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].CO.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:20][C:18]1([CH3:21])[CH:17]([C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[C:16]2[C:29]([CH3:30])=[C:12]([NH2:11])[C:13]([CH3:32])=[C:14]([CH3:31])[C:15]=2[O:19]1

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 11532042HCID 11532042, compound

Product 1

HCID 106853092,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amineYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
67.5 °C

Procedure

The above-obtained 1-(4-nitrophenyl)-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]diazene (6.0 g) and sodium dithionite (14.6 g) were added to a mixture of methanol (30 mL) and water (30 mL), and the mixture was stirred at 65 to 70° C. for 2 hours under a nitrogen atmosphere. The mixture was cooled to room temperature, and further stirred at 0 to 5° C. for one hour. Precipitated crystals were collected by filtration, and washed with a mixture of methanol and water again to obtained wetted crystals. The wetted crystals were added to a mixture of toluene and 2N aqueous sodium hydroxide. An organic layer was separated and concentrated. The concentrate was recrystallized from a mixture of water and methanol, and the resultant crystals were dried under reduced pressure to obtain the title compound (3.5 g., yield 86%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringfurther stirred at 0 to 5° C. for one hour
  3. customPrecipitated crystals
  4. filtrationwere collected by filtration
  5. washwashed with a mixture of methanol and water again
  6. customto obtained wetted crystals
  7. customAn organic layer was separated
  8. concentrationconcentrated
  9. customThe concentrate was recrystallized from a mixture of water and methanol
  10. customthe resultant crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-500c3e4b7aed4a09be160b652a3a78bb
Source dataset
uspto-grants-2009_04
Patent number
US07521545B2

Reaction notes

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