Hydrochloric Acid → HCID 11217711, compound

HRID 394834Notes

Reaction equation

HRID 394834 reaction equation
C[O-].[Na+].[N+](C(C)C)([O-])=[O:5].[Cl:10][C:11]1[C:12]([CH3:20])=[C:13]([C:16]([Cl:19])=[CH:17][CH:18]=1)[CH2:14]Br.Cl>CO.O>[Cl:10][C:11]1[C:12]([CH3:20])=[C:13]([C:16]([Cl:19])=[CH:17][CH:18]=1)[CH:14]=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3982-NitropropaneHCID 10942334Sodium MethoxideHCID 11459455HCID 11459455, compound

Product 1

HCID 11217711HCID 11217711, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

122.4 g (0.68 mol) of a 30% strength solution of sodium methoxide are dissolved in 1030 ml of methanol, and 56.4 g ( 0.57 mol) of 90% pure 2-nitropropane and 188.5 g (0.52 mol) of 61.6% pure 3,6-dichloro-2-methylbenzyl bromide are then added. The reaction is exothermic to 53° C., and the mixture is then stirred for 90 min. The reaction mixture is poured into 2.5 l of water, the pH is adjusted to pH 7.0 using 10% strength HCl, the mixture is extracted three times with 1 l of ethyl acetate, and the organic phases are combined, washed twice with 500 ml of saturated NaCl solution, dried over Na2SO4 and concentrated under reduced pressure: the 161.0 g of crude product are distilled using a 10 cm column packed with 10 mm Raschig rings. The crystals from the last fractions are filtered. This gives 9.8 g comprising 85.9% of the desired product and 4.5% and 6.9% of isomers. Yield: 9.7%. The residue is distilled over a Spaltrohr column, giving another 3.2 g of 94.3% pure product.

Workup

  1. customis exothermic to 53° C.
  2. extractionthe mixture is extracted three times with 1 l of ethyl acetate
  3. washwashed twice with 500 ml of saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. distillationthe 161.0 g of crude product are distilled
  7. filtrationThe crystals from the last fractions are filtered
  8. distillationThe residue is distilled over a Spaltrohr column

Sources & evidence

ORD record
ord-edd85d26f2f2432fa63e28eb9c77e914
Source dataset
uspto-grants-2003_08
Patent number
US06603017B2

Reaction notes

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