Hydrochloric Acid → 1-(3-Chloro-4-cyclohexylphenyl)ethanone

HRID 1777331Notes

Reaction equation

HRID 1777331 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[C:8]([C:18](=[O:20])[CH3:19])[CH:9]=[CH:10][C:11]=1[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[ClH:21]>O>[Cl:21][C:6]1[CH:7]=[C:8]([C:18](=[O:20])[CH3:19])[CH:9]=[CH:10][C:11]=1[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 234649641-(3-Amino-4-cyclohexylphenyl)ethanoneHCID 23668193Sodium Nitrite

Product 1

HCID 109006461-(3-Chloro-4-cyclohexylphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Solution of sodium nitrite (1.2 g, 0.017 mol) in demineralized water (7 mL) is added to a solution of 1-(3-amino-4-cyclohexylphenyl)ethanone (3.4 g, 0.016 mol) in concentrated hydrochloric acid (34 mL) at 0-5° C. & is allowed to stir for 15 minutes at this temperature. It is then poured into a slurry of cuprous chloride (3.1 g, 0.03 mol) in demineralized water (10 mL) at 60-65° C. & stirred for 30 minutes. The reaction mixture is extracted in ethyl acetate (2×30 mL). Combined organic layer is dried over sodium sulfate and concentrated to get the crude, which is purified using column chromatography (230-400 mesh; toluene:n-hexane, 3:2) to yield 1-(3-chloro-4-cyclohexyl-phenyl)ethanone.

Workup

  1. stirringstirred for 30 minutes
  2. extractionThe reaction mixture is extracted in ethyl acetate (2×30 mL)
  3. dry with materialCombined organic layer is dried over sodium sulfate
  4. concentrationconcentrated
  5. customto get the crude, which
  6. customis purified

Sources & evidence

ORD record
ord-fb8a2227321e4d7d86a9d26328b7a683
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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