Nitric Acid → 4-(2',4'-Dichloro-4-ethyl-biphen-3-yl)-2,2,6,6-tetramethyl-4-nitropyran-3,5-dione

HRID 468206Notes

Reaction equation

HRID 468206 reaction equation
[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:3]=1[C:4]1[CH:5]=[CH:6][C:7]([CH2:22][CH3:23])=[C:8]([CH:10]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[O:13][C:12]([CH3:20])([CH3:19])[C:11]2=[O:21])[CH:9]=1.[N:29]([O-:31])=[O:30].[Na+].[N+]([O-])(O)=O>C(O)(=O)C>[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:3]=1[C:4]1[CH:5]=[CH:6][C:7]([CH2:22][CH3:23])=[C:8]([C:10]2([N+:29]([O-:31])=[O:30])[C:15](=[O:16])[C:14]([CH3:17])([CH3:18])[O:13][C:12]([CH3:19])([CH3:20])[C:11]2=[O:21])[CH:9]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 23668193Sodium NitriteHCID 668235414-(2',4'-Dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione

Product 1

HCID 445178074-(2',4'-Dichloro-4-ethyl-biphen-3-yl)-2,2,6,6-tetramethyl-4-nitropyran-3,5-dioneYield 1,202.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-(2′,4′-dichloro-4-ethylbiphen-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.200 g, 0.478 mmol) in glacial acetic acid (5 ml) is added sodium nitrite (0.0025 g, 0.036 mmol) then fuming nitric acid (0.12 ml). The mixture is stirred at room temperature for 2 hours, then the resulting slurry is poured into ice-water (50 ml). After swirling for 5 minutes the precipitate is filtered, dried, then washed with hexanes to afford 4-(2′,4′-dichloro-4-ethyl-biphen-3-yl)-2,2,6,6-tetramethyl-4-nitropyran-3,5-dione (0.201 g, 91%) as a yellow solid, m.p.=138-140° C.

Workup

  1. waitAfter swirling for 5 minutes
  2. filtrationthe precipitate is filtered
  3. customdried
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-83866d106abc4138af7ddc6b75fcbb5d
Source dataset
uspto-grants-2014_01
Patent number
US08623907B2

Reaction notes

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