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

HRID 1721674Notes

Reaction equation

HRID 1721674 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.O>CN(C=O)C>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[CH2:18][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 145789604-(2-quinolinylmethoxy)BenzaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (3.66 g, 30 mmol) and potassium carbonate (8.24 g, 60 mmol) in DMF (75 mL) was added 2-chloromethylquinoline hydrochloride (6.42 g, 30 mmol), and the resulting solution was stirred at ambient temperature for 16 hours. The reaction mixture was then poured into water (100 mL) and extracted with ethyl acetate (100 mL). The extract was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 2:1 hexane-ethyl acetate to afford 4-(2-quinolylmethoxy)benzaldehyde (5.8 g, 74%) as a crystalline compound.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. dry with materialThe extract was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 2:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-a4c7bd632c3c4e208957db8296d60fb3
Source dataset
uspto-grants-1996_04
Patent number
US05512581

Reaction notes

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