4-Hydroxybenzyl Alcohol → 4-(Quinolin-2-ylmethoxy)benzyl alcohol

HRID 1655046Notes

Reaction equation

HRID 1655046 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1>CN(C)C=O>[N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 203942-(Chloromethyl)quinolineHCID 24758Sodium hydride

Product 1

HCID 287755064-(Quinolin-2-ylmethoxy)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 4-hydroxybenzyl alcohol (14.46 g) in dry dimethylformamide (100 ml) was added dropwise to a stirred suspension of sodium hydride (60% dispersion in oil, 5.6 g), (washed with petroleum spirit 40°-60° C.) in dry dimethylformamide (50 ml) cooled under an atmosphere of nitrogen at 0°-5° C. The mixture was stirred at room temperature for 0.5 hour then re-cooled to 0°-5° C. and a solution of 2-chloromethylquinoline (20.69 g) in dry dimethylformamide (100 ml) added dropwise. The mixture was stirred overnight at room temperature, concentrated in vacuo and diluted with water. The crude product was obtained after cooling and filtration.

Workup

  1. temperaturecooled under an atmosphere of nitrogen at 0°-5° C
  2. temperaturethen re-cooled to 0°-5° C.
  3. stirringThe mixture was stirred overnight at room temperature
  4. concentrationconcentrated in vacuo
  5. additiondiluted with water

Sources & evidence

ORD record
ord-852128af5f5d4ea583cf2f6329790dc4
Source dataset
uspto-grants-1995_04
Patent number
US05410061

Reaction notes

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