2-Chloroethanol → 2-(2-nitrophenoxy)ethanol

HRID 1954661Notes

Reaction equation

HRID 1954661 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[OH-].[Na+].O.Cl[CH2:15][CH2:16][OH:17]>C(O)CCC>[OH:17][CH2:16][CH2:15][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 962WaterHCID 69472-NitrophenolHCID 14798Sodium Hydroxide

Product 1

HCID 27370592-(2-nitrophenoxy)ethanolYield 82%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

10 g (71.88 mmol) 2-nitrophenol A1 and 3.59 g (89.86 mmol) sodium hydroxide were dissolved in 55 ml n-butanol and 5 ml water at 70° C., 6.26 ml (7.52 g, 93.44 mmol) 2-chloroethanol were slowly added drop by drop. This was followed by three days of vigorous stirring at 100° C. After cooling, the reaction mixture was filtrated, the precipitate washed with chloroform and the filtrate reduced. The residue was taken up in chloroform and washed three times with aqueous 10% sodium hydroxide solution. Then the organic phase was dried over sodium sulfate and was concentrated in vacuo. 10.8 g of bright yellow crystals were obtained; yield 82%.

Workup

  1. customat 70° C.
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtrated
  4. washthe precipitate washed with chloroform
  5. washwashed three times with aqueous 10% sodium hydroxide solution
  6. dry with materialThen the organic phase was dried over sodium sulfate
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-0e9a22ae3ae24416ad7ab933bafa35b7
Source dataset
uspto-grants-2000_09
Patent number
US06124135

Reaction notes

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