Reaction #464967

Reaction equation

methyl phenylglyoxylate

toluene

→

methyl 2-phenyl-2-cyclopentyl-2-hydroxy-acetate

Yield 76.9%

Conditions

Workup

1. 1
   workup.ADDITIONwere added successively
2. 2
   Othera reaction temperature of -10-6° C.

Procedure

Using the same method as described for (1) of example 3, raw materials at equal weight were added successively. The difference was using a reaction temperature of -10-6° C. during dropuise addition of the toluene solution of 82 g of methyl phenylglyoxylate to cyclopentadiene Grignard reagent. 90 g of methyl 2-phenyl-2-cyclopentyl-2-hydroxy-acetate was obtained in 76.9% yield, nD25 1.5203, boiling point 82-5° C./0.03 mmHg. Silicagel GF 254 thin layer plate; developer: 1,2-dichloroethane, ultraviolet 254 nm fluorescence localization, main spot: Rf=0.72, without impurity spot.

Source