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A solution of 20 g. 3-(trimethylsilyl)propyl bromide and 33.9 g. ethyl 4-aminobenzoate in 75 ml. hexamethylphosphoramide was stirred at 100° for 18 hr. The cooled reaction was diluted with 100 ml. water, the layers were separated, and the aqueous layer was washed three times 100 ml. portions of methylene chloride. The combined organic solutions were washed with water and brine, dried with anhydrous magnesium sulfate, passed through a pad of hydrous magnesium silicate, and evaporated to 96 g. orange liquid. The liquid was dissolved into 100 ml. ethanol and the product was precipitated with 100 ml. water. The solid was filtered and dried. Crystallization from water-ethanol yielded the title compound as a white solid, m.p. 64°-66° C.

1. customThe cooled reaction
2. additionwas diluted with 100 ml
3. customwater, the layers were separated
4. washthe aqueous layer was washed three times 100 ml
5. washThe combined organic solutions were washed with water and brine
6. dry with materialdried with anhydrous magnesium sulfate
7. customevaporated to 96 g
8. dissolutionThe liquid was dissolved into 100 ml
9. customethanol and the product was precipitated with 100 ml
10. filtrationThe solid was filtered
11. customdried
12. customCrystallization from water-ethanol