Nitrofungin → 4-Nitrocatechol

HRID 2215872Notes

Reaction equation

HRID 2215872 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[OH-:12].[Na+]>>[N+:8]([C:6]1[CH:7]=[C:2]([OH:12])[C:3]([OH:11])=[CH:4][CH:5]=1)([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 12074NitrofunginHCID 14798Sodium Hydroxide

Product 1

HCID 35051094-NitrocatecholYield 84%

Conditions

Temperature
60 °C

Procedure

2-chloro-4-nitro-phenol (64.44 g, 0.4 mole) and 300 ml 4M NaOH solution were refluxed with heating for 6 hours. After cooling down and filtration with vacuuming, the filtrate (crystal) was dissolved in a little warm water (60° C.). The solution was adjusted to pH 2.0 with 10% HCl and cooled down while stirring. After filtration, the filtrate was recrystallized with water to yield 4-nitro-1,2-benzenediol (52.1 g, yield rate 84%).

Workup

  1. temperaturewith heating for 6 hours
  2. temperatureAfter cooling down
  3. filtrationfiltration with vacuuming
  4. dissolutionthe filtrate (crystal) was dissolved in
  5. temperaturecooled down
  6. filtrationAfter filtration
  7. customthe filtrate was recrystallized with water

Sources & evidence

ORD record
ord-427857fcd0a4450cbfee6b3390cfcbde
Source dataset
uspto-grants-2006_09
Patent number
US07109364B2

Reaction notes

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