Reaction #81476

Reaction equation

Phenylmalonic acid

thionyl chloride

cyclohexyl alcohol

→

cyclohexyl hydrogen phenylmalonate

Solvents

ether

Conditions

Workup

1. 1
   TemperatureThe 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
   Temperaturerefluxed for 2 hours
5. 5
   Otherto give an oily product which
6. 6
   Othercrystallized
7. 7
   OtherRecrystallization
8. 8
   Otherwas carried out from a benzene-petroleum ether (40°-60°) mixture
9. 9
   Otherto give a white crystalline product

Procedure

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 benzene-petroleum ether (40°-60°) mixture to give a white crystalline product.

Source