Allyl bromide → Methyl alpha-ethyl-alpha-2-propenylbenzeneacetate

To 15.4 ml of diisopropylamine in 400 ml of dry tetrahydrofuran at -20° to -30° under nitrogen atmosphere was added dropwise with stirring 64.3 ml of a 1.71 M solution of butyllithium in hexane. After stirring 15 min., the mixture was cooled to -70° and a solution of 17.8 g of methyl 2-phenylbutyrate in 100 ml of tetrahydrofuran was added dropwise. After stirring 30 min., a solution of 19.9 ml of allyl bromide in 50 ml tetrahydrofuran was added dropwise; the mixture was stirred and allowed to warm to room temperature overnight. After decomposing with methanol, the reaction mixture was concentrated in vacuo and the residue dissolved in diethyl ether. The ether solution was washed successively with dilute hydrochloric acid, water, dilute sodium bicarbonate, and saturated sodium chloride solution, then dried over anhydrous potassium carbonate and concentrated in vacuo. Distillation of the residue yielded 20.2 g of the title compound as a water-white oil, b.p. 84°-86°/0.45 mm, having the following elemental analysis:

1. temperaturethe mixture was cooled to -70°
2. stirringAfter stirring 30 min.
3. stirringthe mixture was stirred
4. concentrationthe reaction mixture was concentrated in vacuo
5. dissolutionthe residue dissolved in diethyl ether
6. washThe ether solution was washed successively with dilute hydrochloric acid, water, dilute sodium bicarbonate, and saturated sodium chloride solution
7. dry with materialdried over anhydrous potassium carbonate
8. concentrationconcentrated in vacuo
9. distillationDistillation of the residue

ORD-Eintrag

ord-3dceaf1bd6054f02adc274c997239858

Quelldatensatz

uspto-grants-1987_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04707499