Sodium hydride → Phenyl p-(2-pyrrolidinoethoxy)benzoate

Temperature

60 °C

To 300 ml. of DMF were added 107 grams of phenyl p-hydroxybenzoate and 26 grams of sodium hydride (50 percent in oil). The mixture was heated at 60° C. for two hours. To the mixture then were added 67 grams of 1-chloro-2-pyrrolidinoethane, and the mixture was stirred overnight at 85° C. The bulk of the DMF then was evaporated from the mixture. Water was added to the residue, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was concentrated, and the residue was dissolved in a 1:1 mixture of ether and ethyl acetate. The organic solution then was extracted with 2 N hydrochloric acid, and the acid extract was added dropwise to 2 N sodium hydroxide. The resulting mixture was extracted with ethyl acetate, and the ethyl acetate extract was washed and then dried over magnesium sulfate. The ethyl acetate was concentrated to obtain 110 grams of crude phenyl p-(2-pyrrolidinoethoxy)benzoate.

1. customThe bulk of the DMF then was evaporated from the mixture
2. additionWater was added to the residue
3. extractionthe aqueous mixture was extracted with ethyl acetate
4. extractionThe ethyl acetate extract
5. concentrationwas concentrated
6. dissolutionthe residue was dissolved in a 1:1 mixture of ether and ethyl acetate
7. extractionThe organic solution then was extracted with 2 N hydrochloric acid
8. extractionthe acid extract
9. additionwas added dropwise to 2 N sodium hydroxide
10. extractionThe resulting mixture was extracted with ethyl acetate
11. extractionthe ethyl acetate extract
12. washwas washed
13. dry with materialdried over magnesium sulfate
14. concentrationThe ethyl acetate was concentrated

ORD record

ord-883adf4e045249d2ae3a12a5477bbcf5

Source dataset

uspto-grants-1980_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04230862