Reacción #54505

Ecuación de reacción

sulfuric acid

2-methylphenylacetyl chloride

ethyl 3-oxobutanoate

magnesium

→

ethyl 2-acetyl-4-(2-methylphenyl)-3-oxobutanoate

Disolventes

ether

carbon tetrachloride

ether

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThis material was prepared
2. 2
   workup.ADDITIONwas added
3. 3
   Temperaturawithout cooling until the reaction
4. 4
   workup.DISSOLUTIONAfter the resulting precipitate dissolved
5. 5
   Temperaturathe solution was cooled in an ice-salt bath
6. 6
   OtroThe ether layer was separated
7. 7
   Lavadowashed with water
8. 8
   Secadodried over sodium sulfate

Procedimiento

This material was prepared according to the procedure of M. Viscontini and N. Merckling, Helvetica Chimica Acta, 35, 2280 (1952). To 2.65 parts of magnesium turnings was added 15 parts absolute ethanol at room temperature and 0.5 parts of carbon tetrachloride. As soon as the initial reaction subsides 100 parts of dry ether was added. The mixture was stirred without cooling until the reaction ceased, then 19.6 parts of ethyl 3-oxobutanoate in 20 parts of dry ether was added with ice cooling and good stirring. After the resulting precipitate dissolved, the solution was cooled in an ice-salt bath and 16 parts of 2-methylphenylacetyl chloride was slowly added. The mixture was allowed to stand overnight at room temperature and then combined with ice and sulfuric acid. The ether layer was separated, washed with water, dried over sodium sulfate and stripped to give ethyl 2-acetyl-4-(2-methylphenyl)-3-oxobutanoate as a crude oil.

Fuente