Potassium Iodide → HCID 14349134, compound

HRID 414839Notes

Reaction equation

HRID 414839 reaction equation
[OH:1][CH:2]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)[CH3:3].Cl[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.O>[OH:1][CH:2]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)[CH3:3]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 135428863-Hydroxyphenylmethylcarbinol

Product 1

HCID 14349134HCID 14349134, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 3-(1-hydroxyethyl)phenol (7 g), 2-chloromethylquinoline (9 g), potassium carbonate (7 g) and potassium iodide (0.3 g) in acetone (75 ml) was refluxed overnight. The reaction mixture was poured into water, and then thoroughly extracted with ethyl acetate (3×30 ml). The organic extract was washed with NaOH solution (1N), water, brine, and then dried over MgSO4. All volatiles were removed to obtain a dark brown liquid, which was chromatographed on silica gel (12% ethyl acetate in hexanes) to leave the desired product as a light yellow liquid.

Workup

  1. temperaturewas refluxed overnight
  2. extractionthoroughly extracted with ethyl acetate (3×30 ml)
  3. extractionThe organic extract
  4. washwas washed with NaOH solution (1N), water, brine
  5. dry with materialdried over MgSO4
  6. customAll volatiles were removed
  7. customto obtain a dark brown liquid, which
  8. customwas chromatographed on silica gel (12% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4e18809fb70840bc9e0e15bcdbf9c8d4
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

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