Pyridine → Benzene, 1-(2-chloroethyl)-2-nitro-

HRID 1859216Notes

Reaction equation

HRID 1859216 reaction equation
N1C=CC=CC=1.S(Cl)([Cl:9])=O.[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21]O)([O-:13])=[O:12].C1(C)C=CC=CC=1>C(Cl)(Cl)Cl>[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][Cl:9])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 24386Thionyl ChlorideHCID 270542-Nitrophenethyl alcohol

Product 1

HCID 11030510Benzene, 1-(2-chloroethyl)-2-nitro-Yield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.1 ml abs. pyridine and 21.62 g thionyl chloride (13.3 ml,. 0.18 mol) is added to 10.13 9 2-(2-nitrophenyl)ethanol (60 mmol) in 36 ml abs. toluene. After 2 h reflux, this is cooled and poured onto ice. The ice water is mixed with 50 ml chloroform and extracted 2× each with 50 ml chloroform. The combined organic phases are neutralized 2× each with 100 ml saturated bicarbonate solution. After drying with Na2SO4, this is filtered and rotary evaporated. After distillation under high-vacuum, 9.7 9 (50 mmol,. 87%) 2-(2-nitrophenyl)ethyl chloride is obtained as a yellow oil with a boiling point of 66 to 67° C. (0.001 mbar).

Workup

  1. temperatureAfter 2 h reflux
  2. temperaturethis is cooled
  3. additionpoured onto ice
  4. extractionextracted 2× each with 50 ml chloroform
  5. dry with materialAfter drying with Na2SO4
  6. filtrationthis is filtered
  7. distillationAfter distillation under high-vacuum

Sources & evidence

ORD record
ord-3762e9a8787142ef847b3c5c10053b91
Source dataset
uspto-grants-2000_11
Patent number
US06153744

Reaction notes

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