3-Hydroxybenzyl alcohol → {3-[3-(Dimethylamino)propoxy]phenyl}methanol

HRID 907252Notes

Reaction equation

HRID 907252 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][CH2:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1.Cl.Cl[CH2:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22].O>CN(C=O)C>[CH3:22][N:21]([CH3:23])[CH2:20][CH2:19][CH2:18][O:15][C:11]1[CH:10]=[C:9]([CH2:8][OH:7])[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1023-Hydroxybenzyl alcoholHCID 962WaterHCID 10796Cesium carbonateHCID 943083-(Dimethylamino)propyl chloride hydrochloride

Product 1

HCID 24229604{3-[3-(Dimethylamino)propoxy]phenyl}methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Cesium carbonate (15.4 g) was added to a solution of 3-hydroxymethyl-phenol (3 g) in DMF (80 mL). To this mixture was added (3-chloro-propyl)-dimethyl-amine hydrochloride (4 g). The mixture was heated at 80° C. for 20 hours then allowed to cool. The reaction mixture was poured into water and extracted with ethyl acetate.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-71e4c966cb49405586c71b9ed62f7d0b
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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