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

HRID 1110893Notes

Reaction equation

HRID 1110893 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>[OH:19][CH2:18][C:17]1[CH:16]=[C:15]([CH:22]=[CH:21][CH:20]=1)[O:14][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

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

20.0 g (93.5 mmoles) of 2-chloromethylquinoline hydrochloride, 11.6 g (93.5 mmoles) of 3-hydroxybenzylalcohol 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 2-(3-hydroxymethylphenoxy)methylquinoline.

Workup

  1. customthe resulting solid is collected
  2. customdried

Sources & evidence

ORD record
ord-a8c6568c85214f64872d0b0f7f8d5a47
Source dataset
uspto-grants-1990_12
Patent number
US04977162

Reaction notes

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