Myristyl bromide → HCID 19389161, compound

HRID 1757848Notes

Reaction equation

HRID 1757848 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-3e0d02c905384ac4832f4b5af49ec246
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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