Hydrochloric Acid → 1-(3-Bromo-4-cyclohexyloxy-phenyl)-hexan-2-one

HRID 402002Notes

Reaction equation

HRID 402002 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](/[CH:8]=[C:9](/[N+]([O-])=O)\[CH2:10][CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.Cl.C[OH:26]>[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9](=[O:26])[CH2:10][CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 673721002-bromo-1-cyclohexyloxy-4-((E)-2-nitro-hex-1-enyl)-benzene

Product 1

HCID 673736281-(3-Bromo-4-cyclohexyloxy-phenyl)-hexan-2-one

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

2-Bromo-1-cyclohexyloxy-4-((E)-2-nitro-hex-1-enyl)-benzene (8.3 mmol, 3.2 g), and iron powder (41.8 mmol, 2.3 g) were dispersed in methanol (20 mL), 3.0 N HCl (20 mL) and heated to reflux for 3.0 h. Cooled the reaction mixture to room temperature, filtered through celite washed with ether. Organic layer separated, dried (Na2SO4) filtered and concentrated under reduced pressure to provide 1-(3-Bromo-4-cyclohexyloxy-phenyl)-hexan-2-one (2.5 g).

Workup

  1. temperatureto reflux for 3.0 h
  2. filtrationfiltered through celite
  3. washwashed with ether
  4. customOrganic layer separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ba8fa05709194d198a384db51d42ff75
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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