2-Methoxyethanol → (2,6-Dichloro-4-nitrophenyl)methanol

HRID 746044

Reaction equation

HRID 746044 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([Cl:13])[C:3]=1[CH2:4]Cl.C[O:15]CCO>O.C(=O)([O-])[O-].[Ag+2]>[Cl:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([Cl:13])[C:3]=1[CH2:4][OH:15]

Participants

5

Reactant 2

HCID 80192-MethoxyethanolHCID 233113981,3-Dichloro-2-(chloromethyl)-5-nitrobenzene

Product 1

HCID 23311409(2,6-Dichloro-4-nitrophenyl)methanol

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 962WaterSolvent

Procedure

A suspension of silver carbonate (560 mg), 2,6-dichloro-4-nitrobenzylchloride (440 mg) in 2-methoxyethanol (9 cm3) and water (9 cm3) were heated at reflux for 18 h. After this time the hot reaction mixture was filtered and the filtrate diluted with dichloromethane (30 cm3) and water (20 cm3). The heterogeneous mixture was shaken, separated and the aqueous phase extracted with dichloromethane (30 cm3). Combined organic extracts were washed with saturated brine, dried and evaporated to leave an orange oil which was purified by chromatography over silica gel with an ethyl acetate--petroleum ether gradient. The title compound was obtained as a cream solid, m.p. 111°-114° C.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 18 h
  3. filtrationAfter this time the hot reaction mixture was filtered
  4. additionthe filtrate diluted with dichloromethane (30 cm3) and water (20 cm3)
  5. customseparated
  6. extractionthe aqueous phase extracted with dichloromethane (30 cm3)
  7. washCombined organic extracts were washed with saturated brine
  8. customdried
  9. customevaporated
  10. customto leave an orange oil which
  11. customwas purified by chromatography over silica gel with an ethyl acetate

Sources & evidence

ORD record
ord-174733046eac4f19baa689f57b0add30
Source dataset
uspto-grants-1986_07
Patent number
US04602041

Linked notes

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