Water → HCID 85768136, compound

HRID 1110296Notes

Reaction equation

HRID 1110296 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](O)[C:7](=[CH:9][CH:10]=1)O)([O-:3])=[O:2].N1C=CC=CC=1.C(Cl)(=[O:28])CCCCCCCCC.O>C(Cl)Cl.C1COCC1>[O:28]=[C:10]1[CH:9]=[CH:7][CH:6]=[CH:5][CH:4]1[N+:1]([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 66982Decanoyl chlorideHCID 35051094-Nitrocatechol

Product 1

HCID 85768136HCID 85768136, compoundYield 323.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred, ice bath cooled solution of 1.0 g (6.45 mmol) of 4-nitrocatechol and 2 ml of pyridine in 25 ml of methylene chloride and 5 ml of THF under argon was added 3.2 ml (15.5 mmol) of decanoyl chloride in 5 ml of THF. The reaction mixture was allowed to warm to room temperature and stirred for 18 hours when it was poured into water and extracted with methylene chloride. The dried extract was concentrated to an oil which was purified by chromatography on 70 g of silica gel using 5% ethyl acetate-hexane to give 2.9 g (97% yield, mp 45°-47°) of 3,4-bis-[(1-oxo]nitrobenzene.

Workup

  1. extractionextracted with methylene chloride
  2. extractionThe dried extract
  3. concentrationwas concentrated to an oil which
  4. customwas purified by chromatography on 70 g of silica gel using 5% ethyl acetate-hexane

Sources & evidence

ORD record
ord-e55c1c04417442168915c71ae98eea48
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

Loading…