2-Methoxyethanol → HCID 58683709, compound

HRID 1991070Notes

Reaction equation

HRID 1991070 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][C:3]=1Cl.[Na].[CH3:14][O:15][CH2:16][CH2:17][OH:18]>>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][C:3]=1[O:18][CH2:17][CH2:16][O:15][CH3:14]

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 3437951,2-Dichloro-4-methyl-5-nitrobenzeneHCID 5360545Sodium

Product 1

HCID 58683709HCID 58683709, compoundYield 63%

Conditions

Temperature
100 °C

Procedure

1,2-Dichloro-4-methyl-5-nitrobenzene (R.J. De Lang, et al. Tetrahedron (1998), 54(12), 2953-2966.) (860 mg; 4.17 mmol) was added to solution of sodium (115 mg; 5.01 mmol) dissolved in 2-methoxyethanol (15 ml). The brown reaction mixture was stirred at 100° C. for 1 h, poured on brine (50 ml) and extracted with TBME three times. The combined organic phases were evaporated and purified via chromatography (SiO2 acetone/hexanes 1/9) to yield the title compound as orange crystals (640 mg; 63%)

Workup

  1. additionpoured on brine (50 ml)
  2. extractionextracted with TBME three times
  3. customThe combined organic phases were evaporated
  4. custompurified via chromatography (SiO2 acetone/hexanes 1/9)

Sources & evidence

ORD record
ord-b027a4d21b364eb388f2825aa5441cd1
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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