Thionyl Chloride → 2-(1-Chloro-2-methyl-2-nitropropyl)naphthalene

HRID 1349436Notes

Reaction equation

HRID 1349436 reaction equation
[CH3:1][C:2]([N+:16]([O-:18])=[O:17])([CH3:15])[CH:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)O.S(Cl)([Cl:21])=O>O>[Cl:21][CH:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)[C:2]([CH3:15])([N+:16]([O-:18])=[O:17])[CH3:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 126400842-Methyl-1-(naphthalen-2-YL)-2-nitropropan-1-OL

Product 1

HCID 223824212-(1-Chloro-2-methyl-2-nitropropyl)naphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2-methyl-1-(naphthalen-2-yl)-2-nitropropanol (1.23 g) obtained in Step 3 was added thionyl chloride (3.1 ml), and the resulting mixture was heated under reflux for 1 hr, and stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure and the residue thus obtained was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=93:7). Recrystallization from a solution of n-hexane:ethyl acetate=4:1, yielded title compound (776 mg).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue thus obtained
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed successively with water and saturated aqueous sodium hydrogencarbonate solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=93:7)
  10. customRecrystallization from a solution of n-hexane

Sources & evidence

ORD record
ord-a5df0bb5c1d648f0a4074f8d455757d0
Source dataset
uspto-grants-2007_05
Patent number
US07211685B2

Reaction notes

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