ChemicalBook CAS DataBase List 5,5-dimethylcyclohex-2-en-1-one

5,5-dimethylcyclohex-2-en-1-one synthesis

12synthesis methods

Product Name:5,5-dimethylcyclohex-2-en-1-one
CAS Number:4694-17-1
Molecular formula:C8H12O
Molecular Weight:124.18

2-Cyclohexen-1-one, 5,5-dimethyl-3-(2-methylpropoxy)-

15466-96-3
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4694-17-1
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Yield:4694-17-1 95%

Reaction Conditions:

Stage #1: 3-isobutoxy-5,5-dimethylcyclohex-2-en-1-onewith lithium aluminium tetrahydride in diethyl ether at 20; for 3 h;
Stage #2: with hydrogenchloride in water at 0;

Steps:

Synthesis of enone via a Stork-Danheiser sequence (11)

General procedure: To a cooled suspension of LiAlH4 (77.5 mg, 2.04 mmol, 0.4 eq.) in the anhydrous diethyl ether (20 mL) the solution of isobutyl vinylogous ester (1.0 gm, 5.09 mmol, 1.0 eq.) in diethyl ether (10 mL) was added dropwise. The mixture was stirred at room temperature for 3 h. After 3 h the reaction mixture was allowed to cool to 0 °C and 1(N) aqueous HCl (5 mL) was added carefully. The ethereal layer was separated, washed with saturated Na2CO3 solution, brine and dried over anhydrous MgSO4. The crude product was purified by column chromatography (hexane-ethyl acetate, 9:1) to afford 11 as a colorless oil (600 mg, 95% yield).

References:

Khatua, Arindam;Shaw, Kundan;Bisai, Vishnumaya [Tetrahedron Letters,2020,vol. 61,# 14,art. no. 151736] Location in patent:supporting information

17530-69-7 Synthesis