Resorcinol → Phenol, 3-(2-quinolinylmethoxy)-

HRID 235984Notes

Reaction equation

HRID 235984 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[C:14]1([CH:21]=[CH:20][CH:19]=[C:17]([OH:18])[CH:16]=1)[OH:15].[OH-].[K+]>C(O)C>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][O:15][C:14]1[CH:16]=[C:17]([OH:18])[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 14797Potassium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 10988736Phenol, 3-(2-quinolinylmethoxy)-Yield 26.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 15.0 g (70.1 mm) of 2-chloromethylquinoline hydrochloride and 7.71 g (70.1 mm) of resorcinol in 50 ml ethanol under nitrogen is added over 30 minutes dropwise a solution of 9.1 g (140.0 mm) potassium hydroxide in 50 ml ethanol. After addition is complete the reaction mixture is refluxed for 2 hours. The solution is allowed to come to room temperature; the precipitate is then filtered off. The mother liquor is evaporated and the residue is triturated with methylene chloride. Evaporation of the organic solvent gives 10.0 g of crude product. HPLC purification affords 4.6 g of a white solid which when recrystallized from toluene affords white crystals, m.p. 153°-155° C.

Workup

  1. additionAfter addition
  2. temperatureis refluxed for 2 hours
  3. customto come to room temperature
  4. filtrationthe precipitate is then filtered off
  5. customThe mother liquor is evaporated
  6. customthe residue is triturated with methylene chloride
  7. customEvaporation of the organic solvent
  8. customgives 10.0 g of crude product
  9. customHPLC purification

Sources & evidence

ORD record
ord-c87730f00eb4435cb71ba6ede87c9060
Source dataset
uspto-grants-1987_02
Patent number
US04642347

Reaction notes

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