5-Chloro-1-indanone

White Crystal

DryPowder

In a thermometer, 500mL four-neck flask with a stirrer and a condensation device Et3NHCl-1.8AlCl3 50 g ionic liquid (molar ratio 1.8), and 50 g of n-octane, raising the temperature to 70-80 deg.] C under stirring.A solution of 100 g of 3-chloro-1- (4-chlorophenyl) -1-propanone and 100 g of n-octane was slowly added, Raise the temperature to 110-120 ° C, Insulation reaction 3-4 hours, The generated hydrogen chloride gas is withdrawn from the top of the condenser tube and enters the water absorption column for absorption, The reaction process uses chromatographic tracking, The content of 3-chloro-1- (4-chlorophenyl) -1-propanone did not decrease, After the reaction was completed, the material was pumped to a 1000 mL jacketed hydrolysis kettle, Stirring slowly adding 100 grams of water for hydrolysis, The hydrolysis kettle is cooled with circulating water, The feed was maintained at a temperature between 90-95 , After that, Stop stirring, Liquid into the separatory funnel, Standing to separate the water phase, N-octane phase into the decolorization tank, Conventional decolorization of the material into the crystallization kettle, Cooling to 0-30 ° C crystallization, Centrifugal treatment, drying, That is, 5-chloro-1-indanone finished product 72 grams.The melting point of 92.6-93.5 , 72percent yield.C. 143.2 g of the organic phase obtained in step B, added to 200 g of dichloromethane, and then added dropwise at 35-40 ° C150.1g of thionyl chloride, after the completion of the dropwise addition for 1h, GC control shows the end point, desolvate the concentrated solution of acid chloride; take another reactionBottle, add 172.1g aluminum trichloride and 300g dichloromethane respectively, the internal temperature drops to 0 ° C, then add the acid chloride concentrate, drop within 3hAt the end, the internal temperature is controlled at 0-10 °C, the GC control shows the end point, and 200 g of 5percent aqueous HCl solution is added dropwise to quench the reaction.The liquid and the separated organic layer are desolvated, dissolved in 100 g of ethanol, and then cooled to -20 ° C to precipitate a yellow solid, solid-liquid separation and drying.Weigh 121.5 g, purity 98.5percent, melting point 91.5-96 ° C, yield 92.6percent.In a 500-ml four-necked flask equipped with a tail-aspiration device, 200 g of anhydrous hexafluoroisopropanol and 0.04 g of anhydrous aluminum trichloride were added; 40 g of m-chlorophenylpropionyl chloride was slowly added dropwise at room temperature at 20° C. within 1 hour. After completion of the dropwise addition, the temperature is raised to 30°C and the reaction is maintained for 2 hours, and then the temperature is raised to 40°C. The reaction is maintained for 2 hours until the conversion of the acid chloride is complete, no hydrogen chloride tail gas is released, and the reaction is stopped;After room temperature, the solution was degassed under a negative pressure to remove hexafluoroisopropanol to obtain 29.7 g of 5-chloro-1-indanone in a yield of 91percent.General procedure: Caution. tert-Butyl hydroperoxide is an exceptionally dangerous chemical that is highly reactive, flammable, and toxic. It is corrosive to skin and mucous membranes and causes respiratory distress when inhaled. A solution of secondary alcohol (1 mmol) and 70percent TBHP (6 or 10 equiv.) was stirred at 100 °C for 24 h. The reaction mixture was quenched with the saturated solution of sodium thiosulfate (5 mL) and extracted with dichloromethane (3 x 10 mL). The combined dichloromethane extracts were dried over anhydrous Na

Intermediates

Molecular Weight:166.60
XLogP3:2.3
Hydrogen Bond Acceptor Count:1
Exact Mass:166.0185425
Monoisotopic Mass:166.0185425
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:178
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes