Water → HCID 19389002, compound

HRID 1757853Notes

Reaction equation

HRID 1757853 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:11])[C:7](=[CH:9][CH:10]=1)[OH:8])([O-:3])=[O:2].N1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:18](Cl)(=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[OH2:30]>C(Cl)Cl.C1COCC1>[O:30]=[C:13]([O:11][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=[CH:9][C:7]=1[O:8][C:18](=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:9][CH2:10][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 66982Decanoyl chlorideHCID 35051094-Nitrocatechol

Product 1

HCID 19389002HCID 19389002, compoundYield 97%

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 in5 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 waspurified 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-oxodecyl)oxy]nitrobenzene.

Workup

  1. extractionextracted with methylene chloride
  2. extractionThe dried extract
  3. concentrationwas concentrated to an oil which

Sources & evidence

ORD record
ord-baee3c21a905490787f3b8064e67c241
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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