Water → HCID 54054639, compound

HRID 1757788Notes

Reaction equation

HRID 1757788 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])([O-:3])=[O:2].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:17]([O:14][C:13]([C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:8]([C:9]([O:11][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])=[O:10])[CH:7]=1)=[O:15])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 120695-Nitroisophthalic acid

Product 1

HCID 54054639HCID 54054639, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (4.7 mmol) of 5-nitroisophthalic acid, 3.1 ml (10.3 mmol) of 1-bromotetradecane and 2.0 g (15 mmol) of potassium carbonate in 40 ml of anhydrous DMF was stirred and heated at 100° for 20 hours.Water was added to the cooled reaction mixture and the resultant solid was filtered and recrystallized from methylene chloride-methanol to give 2.1 g(74% yield, mp 60°-61°) of 5-nitro-1,3-benzenedicarboxylic acid ditetradecyl ester.

Workup

  1. temperatureheated at 100° for 20 hours
  2. filtrationthe resultant solid was filtered
  3. customrecrystallized from methylene chloride-methanol

Sources & evidence

ORD record
ord-8bb3cfb812274c3b95b954a73cc29270
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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