Catechol → Nitrocatechol

HRID 1487197Notes

Reaction equation

HRID 1487197 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[N+:9]([O-])([OH:11])=[O:10]>CCOCC>[N+:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:1]([OH:2])[C:3]=1[OH:4])([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 289CatecholHCID 944Nitric Acid

Product 1

HCID 4675622NitrocatecholYield 30%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of pyrocatechol (60 g, 0.54 mol) in ether (2000 mL) at 0° C. was added fuming nitric acid (24 mL) dropwise. After the addition was over, the reaction was allowed to stand at room temperature for 20 minutes, decanted into ice-water and the resulting solution was extracted with ether. The combined organic extracts were neutralized with aqueous sodium carbonate (10%), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue obtained was purified by silica gel column chromatography (petroleum ether/ethyl acetate 5/1) to afford the product 3-nitrobenzene-1,2-diol (25 g, yield 30%). 1H NMR (400 MHz, CDCl3) δ ppm 10.62 (s, 1H), 7.64-7.67 (dd, 1H, J=1.6 Hz, 8.8 Hz), 7.23-7.26 (m, 1H), 6.89-6.93 (t, 1H, J=8.4 Hz), 5.79 (br, 1H).

Workup

  1. additionAfter the addition
  2. customdecanted into ice-water
  3. extractionthe resulting solution was extracted with ether
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography (petroleum ether/ethyl acetate 5/1)

Sources & evidence

ORD record
ord-a1ece7b88b754e3b8f63eb2a4cd6daa0
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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