Water → 1-[3-(1-Ethoxyethoxy)-4,4,4-trifluorobutoxy]-4-nitrobenzene

HRID 1614371Notes

Reaction equation

HRID 1614371 reaction equation
[H-].[Na+].[CH2:3]([O:5][CH:6]([O:8][CH:9]([C:13]([F:16])([F:15])[F:14])[CH2:10][CH2:11][OH:12])[CH3:7])[CH3:4].Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.O>C1COCC1.CN(C=O)C>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([O:12][CH2:11][CH2:10][CH:9]([O:8][CH:6]([O:5][CH2:3][CH3:4])[CH3:7])[C:13]([F:14])([F:15])[F:16])=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 74741-Chloro-4-nitrobenzeneHCID 24758Sodium hydrideHCID 542222HCID 542222, compound

Product 1

HCID 197736901-[3-(1-Ethoxyethoxy)-4,4,4-trifluorobutoxy]-4-nitrobenzeneYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2.4 g (0.049 mol) of 50% NaH in 50 ml of THF, is slowly added a solution of 10.6 g (0.049 mol) of 3-(1-ethoxyethoxy)-4,4,4-trifluoro-1-butanol in 15 ml of THF. When no more gas evolves, a solution of 6.5 g (0.041 mol) of 4-chloronitrobenzene in 65 ml of DMF is added. After 30 min., the reaction medium is poured on iced water. The reaction medium is extracted with ether. The organic phase is washed with water, dried over Na2SO4 and concentrated. The aimed product is obtained with a 78% yield after recrystallization from isopropanol. m.p.: 81° C;

Workup

  1. extractionThe reaction medium is extracted with ether
  2. washThe organic phase is washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c5f1428ce23841409d6c1a93e02fa55f
Source dataset
uspto-grants-1993_03
Patent number
US05196543

Reaction notes

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