Reacción #65181

Ecuación de reacción

Phenylmalonic acid

thionyl chloride

cyclohexyl alcohol

→

cyclohexyl hydrogen phenylmalonate

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated at 40°-50° C. for 3 hours
2. 2
   workup.DISTILLATIONThe clear solution was distilled under vacuum
3. 3
   workup.DISSOLUTIONThe oily residue was redissolved in dry ether (40 mL)
4. 4
   Temperaturarefluxed for 2 hours
5. 5
   Otroto give an oily product which
6. 6
   Otrocrystallized
7. 7
   OtroRecrystallization
8. 8
   Otrowas carried out from a benzenepetroleum ether (40°-60°) mixture
9. 9
   Otroto give a white crystalline product

Procedimiento

Phenylmalonic acid (13.5 g, 0.07 mol) in dry ether (40 mL) was treated with thionyl chloride (8.92 g, 5.4 mL, 0.07 mol) and one drop of N,N-dimethylformamide. The mixture was heated at 40°-50° C. for 3 hours. The clear solution was distilled under vacuum. The oily residue was redissolved in dry ether (40 mL), the solution was treated with cyclohexyl alcohol (0.075 mol, 7.9 mL) and refluxed for 2 hours. The mixture was worked up as before to give an oily product which crystallized on standing. Recrystallization was carried out from a benzenepetroleum ether (40°-60°) mixture to give a white crystalline product.

Fuente