Quinoline → 3-Chloro-4-cyclohexylethynylbenzene

HRID 426810Notes

Reaction equation

HRID 426810 reaction equation
[Cl:1][C:2]1C=[C:4](C#CC(O)=O)[CH:5]=[CH:6][C:7]=1C1CCCCC1.N1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:20]=1[C:21]#[C:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 129398543-Chloro-4-cyclohexylphenylpropiolic acid

Product 1

HCID 572867553-Chloro-4-cyclohexylethynylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-chloro-4-cyclohexylphenylpropiolic acid (7.3 g.) is heated at 120°-124° for 5 hours in quinoline. The reaction product is diluted with water and washed thoroughly with dilute hydrochloric acid. This is followed by washing with sodium bicarbonate (10%). The material is passed through a short aluminum (H+) column, eluted with N-hexane to give a fraction free of carbonyl absorption (I.R.). Removal of solvent gives 3-chloro-4-cyclohexylethynylbenzene.

Workup

  1. washwashed thoroughly with dilute hydrochloric acid
  2. washby washing with sodium bicarbonate (10%)
  3. washeluted with N-hexane
  4. customto give a fraction
  5. customfree of carbonyl absorption (I.R.)
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-d3438872ded9439493cb2ab54951bea1
Source dataset
uspto-grants-1979_10
Patent number
US04171373

Reaction notes

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