ChemicalBook CAS DataBase List 1-ADAMANTAN-1-YL-PROPAN-2-ONE

1-ADAMANTAN-1-YL-PROPAN-2-ONE synthesis

15synthesis methods

Product Name:1-ADAMANTAN-1-YL-PROPAN-2-ONE
CAS Number:19835-39-3
Molecular formula:C13H20O
Molecular Weight:192.3

768-90-1 Synthesis

768-90-1
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108-22-5 Synthesis

108-22-5
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19835-39-3
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Yield:19835-39-3 83%

Reaction Conditions:

Stage #1: 1-Adamantyl bromidewith aluminum tri-bromide in dichloromethane at -10; for 0.5 h;
Stage #2: Isopropenyl acetate in dichloromethane at -10; for 0.5 h;

Steps:

1-(1-Adamantyl)propan-2-one (1a).

A solution of 43 g (0.2 mol) of 1-bromoadamantane in 260 mL of methylene chloride was cooled to -10 °C, and 61.9 g (0.23 mol) of aluminum bromide was added. The mixture was stirred for 0.5 h, 44 mL (40 g, 0.42 mol) of isopropenyl acetate was added over a period of 2 h, and the mixture was stirred for 0.5 h, poured onto 200 g of ice, and made weakly alkaline reaction by adding sodium carbonate (106 g, 1 mol) and sodium metabisulfite (38 g, 0.2 mol). The organic layer was separated, and the aqueous layer was extracted with methylene chloride (3 × 50 mL). The extracts were combined with the organic phase, the solvent was distilled off, and the residue was distilled under reduced pressure. Yield 31.9 g (83%).

References:

Novakov;Orlinson;Savel’ev;Potaenkova;Vostrikova;Tarakanov;Nakhod [Russian Journal of General Chemistry,2017,vol. 87,# 12,p. 2762 - 2765][Zh. Obshch. Khim.,2017,vol. 87,# 12,p. 1942 - 1946,5]