Sodium Dithionite → 4,6-Di-tert-butyl-3-nitrobenzene-1,2-diol

HRID 2404745Notes

Reaction equation

HRID 2404745 reaction equation
C1COCC1.O.[C:7]([C:11]1[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:14](=[O:21])[C:13](=[O:22])[C:12]=1[N+:23]([O-:25])=[O:24])([CH3:10])([CH3:9])[CH3:8].[O-]S(S([O-])=O)=O.[Na+].[Na+]>CCOC(C)=O>[C:7]([C:11]1[C:12]([N+:23]([O-:25])=[O:24])=[C:13]([OH:22])[C:14]([OH:21])=[C:15]([C:17]([CH3:18])([CH3:19])[CH3:20])[CH:16]=1)([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 534779ST51001883HCID 21881883Oxolane--water (1/1)

Product 1

HCID 179696104,6-Di-tert-butyl-3-nitrobenzene-1,2-diolYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a separatory funnel was placed THF/H2O (1:1, 400 mL), 4,6-di-tert-butyl-3-nitrocyclohexa-3,5-diene-1,2-dione (4.59 g, 17.3 mmol) and Na2S2O4 (3 g, 17.3 mmol). The separatory funnel was stoppered and was shaken for 2 min. The mixture was diluted with EtOAc (20 mL). The layers were separated and the organic layer was washed with brine, dried over MgSO4 and concentrated to provide 4,6-di-tert-butyl-3-nitrobenzene-1,2-diol (3.4 g, 74%), which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 9.24 (s, 1H), 8.76 (s, 1H), 6.87 (s, 1H), 1.35 (s, 9H), 1.25 (s, 9H).

Workup

  1. customIn a separatory funnel was placed
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-88aa5f7030f845de9558b24af7a1690a
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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