Nitric Acid → 2-Acetyl-7-methoxy-4-nitrobenzofuran

HRID 860034Notes

Reaction equation

HRID 860034 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)(=[O:3])[CH3:2].[N+:15]([O-])([OH:17])=[O:16].C(=O)([O-])[O-].[Na+].[Na+]>C(OC(=O)C)(=O)C>[C:1]([C:4]1[O:5][C:6]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]([N+:15]([O-:17])=[O:16])[C:7]=2[CH:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 39378Ethanone, 1-(7-methoxy-2-benzofuranyl)-

Product 1

HCID 128094812-Acetyl-7-methoxy-4-nitrobenzofuran

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 2-acetyl-7-methoxybenzofuran (4.0 g) in acetic anhydride (50 mL) at 0° C. was added 70% nitric acid (1.5 mL) drop-wise. The mixture was warmed to room temperature and stirred for 3 h then poured into ice-cold saturated sodium carbonate (200 mL). Solid sodium carbonate was added carefully with stirring until basic (pH=8). The mixture was filtered and the solid collected by vacuum filtration. The solid was boiled in 100 mL (methanol) for 1 h, then cooled to 0° C. and filtered to give 2-acetyl-7-methoxy-4-nitrobenzpfuran (2.1 g). 1H NMR (300 MHz) δ 8.29 (d,J=8.9 Hz, 1H), 8.14 (s,1H), 7.00 (d,J=8.9 Hz, 1H), 4.14 (s,3H), 2.68 (s, 3H).

Workup

  1. stirringwith stirring until basic (pH=8)
  2. filtrationThe mixture was filtered
  3. filtrationthe solid collected by vacuum filtration
  4. waitThe solid was boiled in 100 mL (methanol) for 1 h
  5. temperaturecooled to 0° C.
  6. filtrationfiltered
  7. customto give 2-acetyl-7-methoxy-4-nitrobenzpfuran (2.1 g)

Sources & evidence

ORD record
ord-8604b9953d2342fb85079c37b7938617
Source dataset
uspto-grants-2006_12
Patent number
US07153871B2

Reaction notes

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