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CAS No. : | 14472-80-1 | MDL No. : | MFCD11850091 |
Formula : | C12H13ClO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JNBOVWFOTNYTES-UHFFFAOYSA-N |
M.W : | 208.68 | Pubchem ID : | 14617880 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With toluene-4-sulfonic acid In toluene at 60℃; for 6 h; | 2-(4-(4-chlorophenyl)-1-hydroxycyclohexyl)-3,4-dihydronaphthalen-1-(2H)-one (12.0 g, 0.0.034 mol) was charged in a reactor equipped with overhead stirrer, reflux condenser and thermo-pocket. Toluene (200 mL) was added to suspend the material and p-toluene sulfonic acid (0.3 g, 2.5 mol percent) was added to the reaction mass which was then heated to 60 °C and stirred for 6 h. Progress of reaction was monitored on TLC. After completion of reaction, reaction mass was cooled to RT and solvent was evaporated under pressure to obtain residue. To the residue, was added ethyl acetate (150 mL) and washed with sat. NaHC03 soln. and brine followed by evaporation of solvent to give crude product which was further recrystallised from methanol to afford white solid compound (5.3 g, 50 percent yield). The mother liquor obtained after re-crystallisation was subjected to GC analysis wherein both a-tetralone and 4-(4-chlorophenyl) cyclohexanone were identified to be present in approx. 1 : 1 ratio (by respective retention times and AUCs in the mother liquor) and in 50 percent yield. GC retention time: a-tetralone (XII): 17.21 min (Area percent : 46) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | Stage #1: With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; bis(pinacol)diborane In tetrahydrofuran for 12 h; Inert atmosphere; Reflux; Green chemistry Stage #2: With copper dichloride In methanol; water for 6 h; Reflux; Green chemistry |
The crude product 2 (150 g, 0.46 mol) obtained in the previous step was dissolved in anhydrous THF (750 ml)Then joinBiphenyl boronic acid(394.4 g, 1.55 mol),PdCl2 (dppf) (7.5 g, 5percent),Et3N (156.5 g, 1.55 mol),The reaction system was replaced with nitrogen twice,The reaction was heated to reflux for 12 hours.TLC detection reaction is complete,Quenching the reaction with water,After filtering the reaction solution,The filtrate was extracted twice with dichloromethane,Each time 500mL,Combined organic phase,After drying with anhydrous sodium sulfate,Concentrated organic phase,To give 140 g of the intermediate. dissolving the intermediate into methanol (600 mL)Then, 200 mL of an aqueous solution of copper chloride (104.5 g, 0.78 mol) was added,Reflux reaction for 6 hours,TLC detection reaction is complete,Cooled to room temperature,Dichloromethane (500 ml * 2) was extracted twice,Combined organic phase,Add 600ml saturated salt washed,Dried over anhydrous sodium sulfate,Concentrated organic phase,To give the product 4- (4-chlorophenyl) cyclohexanone as compound 3 (32.3 g, 0.15 mol)The yield is about 32percent. |