Reaction #667289

Reaction equation

3-phenoxypropionaldehyde

methylmagnesium

methylmagnesium iodide

hydrochloric acid

→

4-phenoxy-2-butanol

Yield 67.0%

Solvents

diethyl ether

Conditions

Workup

1. 1
   Otherby Grignard reaction
2. 2
   Temperaturewhile maintaining a temperature of not more than 20° C
3. 3
   Otherthe diethyl ether layer was separated from an aqueous layer
4. 4
   WashThe ether layer was washed with an aqueous sodium bicarbonate solution
5. 5
   Washwashed with water
6. 6
   Dryingdried over anhydrous sodium sulfate
7. 7
   Othercondensed under reduced pressure

Procedure

24.9 g of methyl iodide was reacted with 7.26 g of magnesium in 150 ml of anhydrous diethyl ether to obtain methylmagnesium iodide by Grignard reaction. To a solution consisting of 20 g of 3-phenoxypropionaldehyde and 200 ml of anhydrous diethyl ether was added dropwise the methylmagnesium while maintaining a temperature of not more than 20° C. The reaction solution was added with 25 ml of concentrated hydrochloric acid, and then the diethyl ether layer was separated from an aqueous layer. The ether layer was washed with an aqueous sodium bicarbonate solution, washed with water, dried over anhydrous sodium sulfate and then condensed under reduced pressure to obtain 15.0 g of 4-phenoxy-2-butanol having a boiling point of 61° C. to 62° C. at 3 mmHg in a yield of 67%.

Source