Sodium Iodide → 6-Hydroxyhexyl 3,5-dinitrobenzoate

HRID 1922544Notes

Reaction equation

HRID 1922544 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].C(=O)([O-])O.[Na+].[I-].[Na+].Cl[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30]>CN1CCCC1=O.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7]([O:9][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])=[O:8])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 74333,5-Dinitrobenzoic acidHCID 748286-Chloro-1-hexanolHCID 516892Sodium Bicarbonate

Product 1

HCID 129955536-Hydroxyhexyl 3,5-dinitrobenzoateYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

357.70 g (1.686 Mol) of 3,5-dinitrobenzoic acid are suspended in 750 ml of 1-methyl-2-pyrrolidone. The suspension is stirred up to 50° C. 386.36 g (4.599 Mol) of sodium hydrogen carbonate are added and the mixture was heated up to 90° C. 22.50 g (0.150 Mol) of sodium iodide and 204.0 ml (1.533 Mol) of 6-chlorohexanol are added to the reaction mixture which is heated to 100° C. for 1 h. After 1 h of reaction, the reaction is complete and the orange suspension is thrown on 2 l of ice and 1 l of water. The product is filtrated, washed water and dried at 50° C. under vacuum for 24 h to give 425.0 g (91%) of 6-hydroxyhexyl 3,5-dinitrobenzoate as a rose powder.

Workup

  1. temperaturethe mixture was heated up to 90° C
  2. temperatureis heated to 100° C. for 1 h
  3. customAfter 1 h of reaction
  4. filtrationThe product is filtrated
  5. washwashed water
  6. customdried at 50° C. under vacuum for 24 h

Sources & evidence

ORD record
ord-519d897a1da14886bed4a44e34c29825
Source dataset
uspto-grants-2012_05
Patent number
US08173749B2

Reaction notes

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