Reaktion #2299

Reaktionsgleichung

methyl phenoxyacetate

3-chloropropionyl chloride

Aluminium chloride

→

methyl 4-[3-chloropropanoyl]phenoxyacetate

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas removed
2. 2
   workup.ADDITIONwas poured into ice-water (500 ml)
3. 3
   SonstigeThe organic phase was separated
4. 4
   Extraktionthe aqueous portion extracted two times with dichloromethane
5. 5
   WaschenThe combined dichloromethane extracts were washed with water
6. 6
   Trocknenbrine and dried (MgSO4)
7. 7
   SonstigeThe residue, after removal of the solvent in vacuo and trituration with ether

Vorschrift

Aluminium chloride (33.35 g) was added portionwise to a stirred cooled (<0° C.) solution of methyl phenoxyacetate (14.46 ml) and 3-chloropropionyl chloride (9.55 ml) in dichloromethane (500 ml). After the addition the ice-bath was removed and the mixture stirred for 1 hour when it was poured into ice-water (500 ml). The organic phase was separated and the aqueous portion extracted two times with dichloromethane. The combined dichloromethane extracts were washed with water, then brine and dried (MgSO4). The residue, after removal of the solvent in vacuo and trituration with ether gave methyl 4-[3-chloropropanoyl]phenoxyacetate, 22.3 g, as a solid: m.p. 89°-90° C.; NMR (d6DMSO) δ 7.95(2H,d), 7.05(2H,d), 4.92(2H,s), 3.91(2H,t), 3.71(3H,s), 3.49(2H,t); m/e 257(M+H)+ ; calculated for C12H13ClO4 : C, 56.1; H, 5.0. found: C, 55.8; H, 5.1%.

Quelle