Reaction #56392

Reaction equation

Sodium

ethyl dichloroacetate

para-cresol

→

Ethyl 2,2-bis(4-methylphenoxy)acetate

Yield 77.3%

Solvents

diethyl ether

ethanol

ethanol

ethanol

Conditions

Workup

1. 1
   TemperatureThe mixture is heated
2. 2
   Temperatureunder reflux for 20 hours
3. 3
   Temperatureto cool
4. 4
   OtherThe white precipitate obtained
5. 5
   Filtrationis filtered off
6. 6
   Concentrationthe filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C
7. 7
   OtherThe oil thus obtained
8. 8
   Washwashed twice with N sodium hydroxide solution (100 cc each time) and twice with distilled water (100 cc each time)
9. 9
   DryingThe ethereal phase is then dried over anhydrous sodium sulphate
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated to dryness under reduced pressure (20 mmHg) at 40° C

Procedure

Sodium (5.7 g) is dissolved in ethanol (160 cc), and a solution of para-cresol (27 g) in ethanol (20 cc) is added. The mixture is stirred for 1 hour at 20° C. and ethyl dichloroacetate (20 g) in solution in ethanol (20 cc) is then added. The mixture is heated under reflux for 20 hours and then allowed to cool. The white precipitate obtained is filtered off and the filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C. The oil thus obtained is taken up in diethyl ether (300 cc) and washed twice with N sodium hydroxide solution (100 cc each time) and twice with distilled water (100 cc each time). The ethereal phase is then dried over anhydrous sodium sulphate, filtered, and concentrated to dryness under reduced pressure (20 mmHg) at 40° C. Ethyl 2,2-bis(4-methylphenoxy)acetate (29 g) is thus obtained as a yellow oil.

Source