Réaction #56391

Équation de réaction

Sodium

Ethyl 2,2-dichloro-acetate

4-Methoxyphenol

→

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

Rendement 76.7%

Solvants

diethyl ether

ethanol

ethanol

ethanol

ethanol

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONis added
2. 2
   workup.ADDITIONis then added
3. 3
   Températurethe mixture is heated
4. 4
   Températureunder reflux for 20 hours
5. 5
   Autreis driven off under reduced pressure (20 mmHg) at 40° C.
6. 6
   LavageThe organic phase is washed with 0.1 N sodium hydroxide solution (100 cc) and with water (2×100 cc)
7. 7
   Séchageis then dried over sodium sulphate
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated to dryness under reduced pressure (20 mmHg) at 40° C

Mode opératoire

Sodium (5.4 g) is dissolved in absolute ethanol (160 cc). 4-Methoxyphenol (29.2 g) dissolved in absolute ethanol (20 cc) is added. The mixture is stirred for 1 hour at ambient temperature. Ethyl 2,2-dichloro-acetate (20 g) dissolved in absolute ethanol (20 cc) is then added and the mixture is heated under reflux for 20 hours. The ethanol is driven off under reduced pressure (20 mmHg) at 40° C. and the residue is taken up in diethyl ether (100 cc). The organic phase is washed with 0.1 N sodium hydroxide solution (100 cc) and with water (2×100 cc) and is then dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure (20 mmHg) at 40° C. Ethyl 2,2-bis(4-methoxyphenoxy)-acetate (30 g) is thus obtained in the form of an oil.

Source