Reaktion #477971

Reaktionsgleichung

2,4-dichloro-1-chloromethoxy-benzene

mercapto-acetic acid ethyl ester

NaH

→

(2,4-dichloro-phenoxymethylsulfanyl)-acetic acid

Ausbeute 57.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 16 hrs at ambient temperature
3. 3
   SonstigeThe reaction was quenched by addition of water (50 mL)
4. 4
   Extraktionextracted with diethyl ether (2×50 mL)
5. 5
   WaschenThe combined organic phases were washed with saturated aq. ammonium chloride (50 mL)
6. 6
   Trocknendried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated in vacuo
9. 9
   workup.DISSOLUTIONThe residue was dissolved in EtOH (20 mL) and to this solution
10. 10
    workup.ADDITIONwas added aq. 32% NaOH (1 mL) and water (10 mL)
11. 11
    workup.STIRRINGStirring
12. 12
    workup.WAITwas continued for 16 hrs at room temperature
13. 13
    SonstigeThe volatiles were evaporated in vacuo, water (20 mL)
14. 14
    workup.ADDITIONwas added
15. 15
    Waschenby washing with diethyl ether (20 mL)
16. 16
    Extraktionfollowed by extraction with diethyl ether (2×25 mL)
17. 17
    TrocknenThe combined organic phases were dried (Na2SO4)
18. 18
    Filtrationfiltered
19. 19
    Sonstigethe solvent evaporated in vacuo

Vorschrift

To a solution of mercapto-acetic acid ethyl ester (2.4 g, 19.86 mmol) in dry DMF (20 mL) was added NaH (556 mg, 23.27 mmol, 60% in mineral oil). The mixture was stirred for 30 min. at room temperature followed by dropwise addition of 2,4-dichloro-1-chloromethoxy-benzene (3.5 g, 16.55 mmol), stirring was continued for 16 hrs at ambient temperature. The reaction was quenched by addition of water (50 mL) and extracted with diethyl ether (2×50 mL). The combined organic phases were washed with saturated aq. ammonium chloride (50 mL), dried (Na2SO4), filtered and evaporated in vacuo. The residue was dissolved in EtOH (20 mL) and to this solution was added aq. 32% NaOH (1 mL) and water (10 mL). Stirring was continued for 16 hrs at room temperature. The volatiles were evaporated in vacuo, water (20 mL) was added followed by washing with diethyl ether (20 mL). The aqueous phase was acidified to pH˜1 with conc. HCl followed by extraction with diethyl ether (2×25 mL). The combined organic phases were dried (Na2SO4), filtered and the solvent evaporated in vacuo affording 2.5 g (57%) of crude (2,4-dichloro-phenoxymethylsulfanyl)-acetic acid as a solid.

Quelle