Nitric Acid → ST51001883

HRID 2404744Notes

Reaction equation

HRID 2404744 reaction equation
[C:1]([C:5]1[C:6](=[O:16])[C:7](=[O:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N+:17]([O-])([OH:19])=[O:18].O>C(O)(=O)C>[C:11]([C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6](=[O:16])[C:7](=[O:15])[C:8]=1[N+:17]([O-:19])=[O:18])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 769153,5-Di-tert-butyl-1,2-benzoquinone

Product 1

HCID 534779ST51001883Yield 24%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3,5-di-tert-butylcyclohexa-3,5-diene-1,2-dione (4.20 g, 19.1 mmol) in acetic acid (115 mL) was slowly added HNO3 (15 mL). The mixture was heated at 60° C. for 40 min before it was poured into H2O (50 mL). The mixture was allowed to stand at room temperature for 2 h, then was placed in an ice bath for 1 h. The solid was collected and washed with water to provide 4,6-di-tert-butyl-3-nitrocyclohexa-3,5-diene-1,2-dione (1.2 g, 24%). 1H NMR (400 MHz, DMSO-d6) δ 6.89 (s, 1H), 1.27 (s, 9H), 1.24 (s, 9H).

Workup

  1. waitwas placed in an ice bath for 1 h
  2. customThe solid was collected
  3. washwashed with water

Sources & evidence

ORD record
ord-8c5ac0ef0cd74be696b2a942174bc812
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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