Tyrosol → 4-[2-(Cyclopropylmethoxy)ethyl]phenol

HRID 2994

Reaction equation

HRID 2994 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.[CH3:11][C:12]([CH3:15])([O-])[CH3:13].[K+].ClCC1CC1>CS(C)=O>[CH2:11]1[CH2:13][CH:12]1[CH2:15][O:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 10393TyrosolHCID 80013(Chloromethyl)cyclopropaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 110524814-[2-(Cyclopropylmethoxy)ethyl]phenol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
50 °C

Procedure

A reaction flask was charged with 4-Hydroxyphenethyl alcohol (1) (100 g, 0.72 mol), Potassium tert-butoxide (243 g, 2.17 mol), and 500 mL of DMSO. The mixture was stirred under nitrogen at 50° C. for 30 minutes. A solution of (Chloromethyl)cyclopropane (100 g, 1.10 mol) in 500 mL of DMSO was added dropwise to the reaction mixture. The mixture was then stirred at 50° C. for one hour and then cooled to room temperature.

Workup

  1. stirringThe mixture was then stirred at 50° C. for one hour
  2. temperaturecooled to room temperature

Sources & evidence

ORD record
ord-01039e4c25c144fb9c3dd548ff4937c0
Source dataset
uspto-grants-1998_03
Patent number
US05731463

Linked notes

Loading…