3-Hydroxybenzyl alcohol → Benzenemethanol, 3-(2-quinolinylmethoxy)-

HRID 2248875Notes

Reaction equation

HRID 2248875 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:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][OH:19].[OH-].[Na+]>CS(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:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 14798Sodium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 14650410Benzenemethanol, 3-(2-quinolinylmethoxy)-Yield 103.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

20.0g (93.5 mmoles) of 2-chloromethylquinoline hydrochloride, 11.6 g (93.5 mmoles) of 3-hydroxybenzyl alcohol and 7.48 g (186.42 mmoles) of powdered sodium hydroxide are combined in 56 ml of dimethylsulfoxide. After stirring room temperature for 24 hours the mixture is poured into ice-water and the resulting solid is collected and dried to give 25.6 g of 3-(2-quinolinylmethyloxy)benzyl alcohol.

Workup

  1. customthe resulting solid is collected
  2. customdried

Sources & evidence

ORD record
ord-a285d952d4a8416d8756545c786747d3
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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