4-Hydroxybenzaldehyde → 4-(2-quinolinylmethoxy)Benzaldehyde

HRID 1029441Notes

Reaction equation

HRID 1029441 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.[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CCOCC>CC(C)=O>[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:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 145789604-(2-quinolinylmethoxy)Benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture containing 2-(chloromethyl)quinoline hydrochloride (15 g), 4-hydroxybenzaldehyde (8.56 g) and anhydrous potassium carbonate (29 g) was heated under reflux in acetone (300 mL) for 86 h. After cooling to room temperature, ether (400 mL) was added and the mixture was filtered on celite. The filtrate was evaporated to dryness under reduced pressure and purified by flash chromatography using 15% ethyl acetate/hexane. The title compound was obtained after recrystallization from ethyl acetate/hexane m.p. 89°-90°.

Workup

  1. temperaturewas heated
  2. filtrationthe mixture was filtered on celite
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-85be43ac5de24fc7800dbb85d87f1d0d
Source dataset
uspto-grants-1992_04
Patent number
US05102881

Reaction notes

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