Hydrochloric Acid → rac-(2S*)-2-[(R*)-3,4-dichloro-alpha-(nitromethyl)benzyl]cyclohexanone

HRID 620318Notes

Reaction equation

HRID 620318 reaction equation
[CH:1]1[C:6](/[CH:7]=[CH:8]/[N+:9]([O-:11])=[O:10])=[CH:5][C:4]([Cl:12])=[C:3]([Cl:13])[CH:2]=1.[C:14]1(N2CCOCC2)[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=1.Cl.C([O:30]C(C)C)(C)C>C(Cl)Cl>[Cl:12][C:4]1[CH:5]=[C:6]([CH:1]=[CH:2][C:3]=1[Cl:13])[C@@H:7]([CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][C:14]1=[O:30])[CH2:8][N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 69589Morpholine, 4-(1-cyclohexen-1-yl)-HCID 53722591,2-Dichloro-4-[(E)-2-nitroethenyl]benzene

Product 1

HCID 53781409rac-(2S*)-2-[(R*)-3,4-dichloro-alpha-(nitromethyl)benzyl]cyclohexanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 52.3 g (0.24 mol) of 3,4-dichloro-ω-nitrostyrene in 500 ml of methylene chloride is added while stirring and cooling within about 45 minutes to a solution of 40.1 g (0.24 mol) of N-(1-cyclohexen-1-yl)morpholine in 400 ml of methylene chloride under nitrogen so that the temperature does not exceed 0°. The mixture is subsequently stirred at 0° for a further 3 hours. 420 ml of 1N hydrochloric acid are added rapidly while stirring intensively, whereupon the mixture is stirred for a further 30 minutes. The aqueous phase is separated and extracted twice with 500 ml of methylene chloride each time; the organic phase is washed with water, dried over magnesium sulphate and evaporated. The oily residue obtained is taken up in 250 ml of isopropyl ether and left to stand in a refrigerator overnight. There is obtained rac-(2S*)-2-[(R*)-3,4-dichloro-α-(nitromethyl)benzyl]cyclohexanone in the form of colourless crystals of m.p. 109°- 110°.

Workup

  1. customdoes not exceed 0°
  2. stirringThe mixture is subsequently stirred at 0° for a further 3 hours
  3. stirringwhile stirring intensively, whereupon the mixture
  4. stirringis stirred for a further 30 minutes
  5. customThe aqueous phase is separated
  6. extractionextracted twice with 500 ml of methylene chloride each time
  7. washthe organic phase is washed with water
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customThe oily residue obtained
  11. waitleft
  12. customto stand in a refrigerator overnight

Sources & evidence

ORD record
ord-ba7f2f736b6a49aab7aa9cdad2b528d1
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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