Thionyl Chloride → HCID 49764772, compound

HRID 384989Notes

Reaction equation

HRID 384989 reaction equation
[CH3:1][CH:2]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH:3](O)[CH2:4][N+:5]([O-:7])=[O:6].S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1.CN(C)C=O>[Cl:15][CH:3]([CH:2]([CH3:1])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:4][N+:5]([O-:7])=[O:6]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 49764771HCID 49764771, compound

Product 1

HCID 49764772HCID 49764772, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

After dissolving 2.0 g of 3,5-dimethyl-1-nitro-2-hexanol in 15 ml of toluene, 4.1 g of thionyl chloride and two drops of N,N-dimethylformamide were added thereto, and the solution was stirred for 2.5 hours at 80° C. The solution was cooled to room temperature and concentrated, and then purified by silica gel chromatography (hexane/ethyl acetate=8/1), thereby obtaining 1.5 g of 2-chloro-3,5-dimethyl-1-nitrohexane (yield: 72.4%).

Workup

  1. additionwere added
  2. temperatureThe solution was cooled to room temperature
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-0561cf39f2604c5e824a35c6ec9f0393
Source dataset
uspto-grants-2013_02
Patent number
US08367846B2

Reaction notes

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