Water → 1,11-Bis(4-nitrophenoxy)undecane

HRID 477577Notes

Reaction equation

HRID 477577 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-:11].[Na+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.[OH2:26]>CS(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:11][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:2])=[O:26])=[CH:5][CH:6]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 14798Sodium HydroxideHCID 855511,11-Dibromoundecane

Product 1

HCID 198362341,11-Bis(4-nitrophenoxy)undecaneYield 64%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A 4-necked flask, equipped with a mechanical stirring device, a dropping funnel, a reflux condenser and a thermometer, is charged with 8.9 g (65 mmol) of paranitrophenol in 20 ml of dimethylsulphoxide. To this solution there are added 2.56 g (64 mmol) of solid pelletized sodium hydroxide. The resultant mixture is heated to 100° C. on an oil bath, until a homogeneous solution is obtained. To the latter solution there are cautiously added 10 g (32 mmol) of 1,11-dibromoundecane, dissolved in 20 ml of dimethylsulphoxide, and, on completion of this addition, the reaction mixture is held at 100° C. for 2 hours. Finally, the reaction mixture is cooled and poured into one litre of continually stirred water, the result being the formation of a solid precipitate which is collected on a filter and repeatedly washed with water. The washed solid is crystallized from ethyl alcohol and 8.8 g of 1,11-bis(4-nitrophenoxy)undecane is obtained (yield 64%).

Workup

  1. customA 4-necked flask, equipped with a mechanical stirring device, a dropping funnel, a reflux condenser
  2. customis obtained
  3. additionon completion of this addition
  4. temperatureFinally, the reaction mixture is cooled
  5. customis collected on
  6. filtrationa filter
  7. washrepeatedly washed with water
  8. customThe washed solid is crystallized from ethyl alcohol

Sources & evidence

ORD record
ord-7b98588aba2a4f8ea35f29a525d4b63b
Source dataset
uspto-grants-1989_12
Patent number
US04888409

Reaction notes

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