ChemicalBook CAS DataBase List 2,2,4,4-TETRAMETHYLCYCLOPENTANONE

2,2,4,4-TETRAMETHYLCYCLOPENTANONE synthesis

7synthesis methods

Product Name:2,2,4,4-TETRAMETHYLCYCLOPENTANONE
CAS Number:4694-11-5
Molecular formula:C9H16O
Molecular Weight:140.22

Cyclohexanone, 3,3,5-trimethyl-5-(trimethylstannyl)-

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4694-11-5
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Yield:4694-11-5 86.6%

Reaction Conditions:

with titanium tetrachloride in dichloromethane at 0; for 0.333333 h;Inert atmosphere;

Steps:

98.2 Step 2: 2,2,4,4-Tetramethylcyclopentanone

To a stirring solution of 3,3,5-trimethyl-5-trimethylstannyl-cyclohexanone (4.17 g, 13.8 mmol) in the dichloromethane (79.23 mL) under a nitrogen atmosphere at 0° C. was added (dropwise) tetrachlorotitanium (2.610 g, 2.183 mL, 13.76 mmol) giving a dark brown color on addition. Upon completion of addition the reaction mixture was a brown suspension which was stirred 20 minutes at 0° C. and then quenched by the addition of a solution of saturated aqueous sodium bicarbonate (Caution: Gas evolution, reaction became biphasic with a purple suspension as the aqueous layer). The resulting mixture was extracted twice with dichloromethane, dried (magnesium sulfate), filtered and carefully concentrated to a clear oil. Purified by silica gel chromatography eluting with 100% giving 2,2,4,4-tetramethylcyclopentanone (1.67 g, 11.9 mmol, 86.6%) as a clear oil.

References:

US2016/95858,2016,A1 Location in patent:Paragraph 4771; 4772