Acetic Acid → 2,2,4,6,7-Pentamethyl-5-nitro-3-phenyl-2,3-dihydrobenzofuran

HRID 964811Notes

Reaction equation

HRID 964811 reaction equation
C(O)(=O)C.[N+:5]([O-:8])(O)=[O:6].[CH3:9][C:10]1([CH3:28])[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13]2[C:21]([CH3:27])=[CH:22][C:23]([CH3:26])=[C:24]([CH3:25])[C:12]=2[O:11]1>C(OC(=O)C)(=O)C>[CH3:9][C:10]1([CH3:28])[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13]2[C:21]([CH3:27])=[C:22]([N+:5]([O-:8])=[O:6])[C:23]([CH3:26])=[C:24]([CH3:25])[C:12]=2[O:11]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 108017332,2,4,6,7-Pentamethyl-3-phenyl-2,3-dihydrobenzofuran

Product 1

HCID 106628262,2,4,6,7-Pentamethyl-5-nitro-3-phenyl-2,3-dihydrobenzofuranYield 48.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

The mixed solution of acetic anhydride (3 ml) and acetic acid (3 ml) was cooled and nitric acid (3 ml) was added cautiously with stirring. Then a solution of 2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydrobenzofuran (3.7 g, 13.9 mmol) in acetic anhydride (3 ml) was added dropwise and the mixture was stirred for 30 minutes. The reaction mixture was poured into ice-cold water and the product was extracted with ethyl acetate. The extract was washed with saturated sodium bicarbonate solution, dried and concentrated. The residue was purified by column chromatography on silica gel (hexane-isopropyl ether, 9:1) and crystallized from methanol to obtain the desired compound (2.08 g, yield: 48.1%), m.p. 155°-156° C.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. additionThe reaction mixture was poured into ice-cold water
  3. extractionthe product was extracted with ethyl acetate
  4. washThe extract was washed with saturated sodium bicarbonate solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane-isopropyl ether, 9:1)
  8. customcrystallized from methanol

Sources & evidence

ORD record
ord-9c9fba8be003466aaf748e15ae39c524
Source dataset
uspto-grants-1998_06
Patent number
US05770772

Reaction notes

Loading…