Myristyl bromide → HCID 19389161, compound

HRID 1110292Notes

Reaction equation

HRID 1110292 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:11])[C:7](=[CH:9][CH:10]=1)O)([O-:3])=[O:2].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[C:27](=[O:30])([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH2:13]([O:11][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=[CH:9][C:7]=1[O:30][CH2:27][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 35051094-Nitrocatechol

Product 1

HCID 19389161HCID 19389161, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (6.45 mmol) of 4-nitrocatechol, 4.8 ml (16.1 mmol) of 1-bromotetradecane and 2.5 g (17.4 mmol) of potassium carbonate in 20 ml of acetone and 10 ml of DMF was stirred at reflux under argon for 24 hours. The reaction mixture was filtered while hot and the filtrate was allowed to cool to room temperature and 3.5 g (99% yield, mp 64°-66°) of 3,4-bis(tetradecyloxy) nitrobenzene was obtained by filtration. The structure was confirmed by nmr and mass spectra.

Workup

  1. temperatureat reflux under argon for 24 hours
  2. filtrationThe reaction mixture was filtered while hot and the filtrate

Sources & evidence

ORD record
ord-c4ac44c0085a4cff89c80ce92a060e52
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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