Benzyl Bromide → (2-Benzyloxy-5-chloro-phenyl)-methanol

HRID 2356599Notes

Reaction equation

HRID 2356599 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][OH:10])[CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH2:9][OH:10])[CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 792385-Chlorosalicyl alcohol

Product 1

HCID 19317759(2-Benzyloxy-5-chloro-phenyl)-methanolYield 106.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Chloro-2-(hydroxymethyl)phenol (5 g, 31 mmol), benzyl bromide (3.74 ml, 31 mmol), and potassium carbonate (4.78 g, 34 mmol) were refluxed in acetone (30 ml) for two hours. TLC showed no more SM (starting material). Cooled down, filtered off the solid and vacuumed down (the filtrate) to give a clear oil (8.2 g).

Workup

  1. temperatureCooled down
  2. filtrationfiltered off the solid

Sources & evidence

ORD record
ord-3b780a849f664864b3792684e5fa354a
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

Loading…