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

HRID 1708491Notes

Reaction equation

HRID 1708491 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl.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+].O>CN(C=O)C>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[CH2:12][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

A mixture of 4-hydroxybenzaldehyde (3.66 g, 30 mmol),2-chloromethylquinoline hydrochloride (6.42 g, 30 mmol) and potassium carbonate (8.24 g, 60 mmol) in DMF (75 mL) was stirred at ambient temperature for 16 hours. The reaction mixture was then poured into water (300 mL) and extracted with ethyl acetate. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue obtained was chromatographed on silica gel eluting with 1:2 ethyl acetate-hexane to provide 5.8 g (74%) of 4-(2-quinolinyl-methoxy)benzaldehyde.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue obtained
  5. customwas chromatographed on silica gel eluting with 1:2 ethyl acetate-hexane

Sources & evidence

ORD record
ord-c5b192c8610d4ff5ad9949f1d3bc77bb
Source dataset
uspto-grants-1994_10
Patent number
US05358955

Reaction notes

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