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Chemical Structure| 20386-93-0
Chemical Structure| 20386-93-0
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CAS No. :20386-93-0 MDL No. :
Formula : C14H10ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :245.68 Pubchem ID :-
Synonyms :

Safety of [ 20386-93-0 ]

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Application In Synthesis of [ 20386-93-0 ]

* 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.

  • Downstream synthetic route of [ 20386-93-0 ]

[ 20386-93-0 ] Synthesis Path-Downstream   1~8

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YieldReaction ConditionsOperation in experiment
91% With silica gel; iron(III) perchlorate In dichloromethane Heating;
90% Stage #1: benzoic acid With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In neat (no solvent) at 20℃; for 0.0166667h; Stage #2: para-Chlorobenzyl alcohol In neat (no solvent) at 20℃; for 0.0833333h; Generalprocedure for the preparation of esters 3a-n General procedure: A mixture of carboxylic acid (1 mmol) and TAPC (0.5 mmol, 0.17 g) was prepared in a mortar. The mixturewas ground with a pestle for 1 min. Then alcohol (1 mmol) was added to thereaction mixture and grinding was continued at room temperature for appropriatereaction times indicated in Table 1. After completion of the reaction(monitored by TLC), H2O (10 mL) was added to the reaction mixture.The residue was then extracted with EtOAc (4 × 5 mL), and the combined extractswere dried over MgSO4. The filtrate was evaporated, and the esterwas obtained as the only product.
88% With 1H-imidazole; iodine; chloro-diphenylphosphine In acetonitrile for 4.5h; Reflux;
83% With montmorillonite KSF for 0.00833333h; Microwave irradiation; Green chemistry;
82% With triphenylphosphine In acetonitrile for 3.5h; Heating;
67% With nitrobenzene; triphenylphosphine; 3-methyl-2',3',4',5'-tetraacetylriboflavin at 40℃; for 24h; Molecular sieve; Irradiation;
66% With C22H25F3N3O2(1+)*Cl(1-); oxygen; triphenylphosphine In acetonitrile at 50℃; for 48h; Molecular sieve;
43% With di-isopropyl azodicarboxylate; phenylsilane; oxygen; triphenylphosphine; 3-methyl-2',3',4',5'-tetraacetylriboflavin In acetonitrile at 50℃; for 24h; Molecular sieve; Irradiation;
With trimethylamine borane In xylene for 5h; Heating; Yield given;
With 5,5'-dimethyl-3,3′-azoisooxazole; triphenylphosphine In acetonitrile Reflux;
90 %Chromat. With tris(1-glycyl-3-methyl imidazolium chloride-iron(III)) In neat (no solvent) at 25℃; for 6h; Green chemistry;

Reference: [1]Salechi; Khodaei; Ghareghani; Motlagh [Russian Journal of Organic Chemistry, 2003, vol. 39, # 6, p. 794 - 796]
[2]Bahrami, Kiumars; Khodaei, Mohammad M.; Targhan, Homa; Sheikh Arabi, Mehdi [Tetrahedron Letters, 2013, vol. 54, # 37, p. 5064 - 5068]
[3]Location in patent: experimental part Nowrouzi, Najmeh; Mehranpour, Abdol Mohammad; Rad, Javad Ameri [Tetrahedron, 2010, vol. 66, # 50, p. 9596 - 9601]
[4]Marvi; Fekri; Takhti [Russian Journal of General Chemistry, 2014, vol. 84, # 9, p. 1837 - 1840]
[5]Iranpoor, Nasser; Firouzabadi, Habib; Khalili, Dariush; Motevalli, Somayeh [Journal of Organic Chemistry, 2008, vol. 73, # 13, p. 4882 - 4887]
[6]März, Michal; Kohout, Michal; Neveselý, Tomáš; Chudoba, Josef; Prukała, Dorota; Niziński, Stanislaw; Sikorski, Marek; Burdziński, Gotard; Cibulka, Radek [Organic and Biomolecular Chemistry, 2018, vol. 16, # 36, p. 6809 - 6817]
[7]März, Michal; Babor, Martin; Cibulka, Radek [European Journal of Organic Chemistry, 2019, vol. 2019, # 20, p. 3264 - 3268]
[8]März; Chudoba; Kohout; Cibulka [Organic and Biomolecular Chemistry, 2017, vol. 15, # 9, p. 1970 - 1975]
[9]Trapani, Giuseppe; Reho, Antonia; Latrofa, Andrea; Liso, Gaetano [Synthesis, 1990, # 9, p. 853 - 854]
[10]Iranpoor, Nasser; Firouzabadi, Habib; Khalili, Dariush [Organic and Biomolecular Chemistry, 2010, vol. 8, # 19, p. 4436 - 4443]
[11]Karthikeyan, Parasuraman; Bhagat, Pundlik Rambhau; Kumar, Sellappan Senthil; Muskawar, Prashant Narayan; Aswar, Sachin Arunrao [Journal of the Iranian Chemical Society, 2012, vol. 9, # 6, p. 983 - 990]
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YieldReaction ConditionsOperation in experiment
90% Stage #1: para-Chlorobenzyl alcohol With manganese(II) iodide; naphthalene; lithium In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: benzoyl chloride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Phenyl 3-Chlorobenzoate (1c); Typical Procedure General procedure: A 25 mL flask was charged with lithium (0.07 g, 9.68 mmol),naphthalene (0.19 g, 1.48 mmol), anhyd MnI2 (1.45 g, 4.71 mmol), and freshly distilled THF (10 mL) under argon pressure,and the mixture was stirred for 1 h at r.t. To the resultingslurry, containing 2.5 mmol of highly active manganese, wasadded PhOH (0.47 g, 5.0 mmol) and the resulting mixture wasstirred at r.t. for 10 min. Neat 3-chlorobenzoyl chloride (0.88 g,5.0 mmol) was then added to the flask, and the mixture wasstirred at r.t. for 30 min. The reaction was then quenched with3 M aq HCl, and the mixture was extracted with Et2O (3 × 10 mL).The organic layers were combined and washed with sat. aqNaHCO3 (3 × 10 mL), sat. aq Na2S2O3 (3 × 10 mL), and brine (3 ×10 mL), then dried (MgSO4). Column chromatography (silica gel,1% EtOAc-hexanes) gave a pale-yellow solid.yield: 0.96 g (83%).
87% With pyridine at 0℃; for 1.5h;
78% With lithium perchlorate In tetrahydrofuran at 25℃; for 7h;
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YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetone / 16 h / Darkness 2: tolune-d8 / 90 °C
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YieldReaction ConditionsOperation in experiment
66% With tert.-butylhydroperoxide; sodium dihydrogenphosphate; tetra-(n-butyl)ammonium iodide In water; acetonitrile at 80℃; for 36h; Schlenk technique; General procedure for the aerobic oxidative esterificationreactions General procedure: Alcohol (0.50 mmol), hydrocarbon (10 mmol, 20 equiv), NaH2PO4 (74 mg, 97%, anhydrous, 0.6mmol, 1.2 equiv), Bu4NI (36.9 mg, 0.10mmol, 20 mol %), TBHP (70% aqueous solution, 0.42 mL,3.0 mmol, 6 equiv) and MeCN (2 mL) were added into a Schlenk flask with a high vacuum valve (V = 45 mL) fitting in a Radleys parallel synthesis station.1 The solution was stirred vigorously and heated at 80 oC for 36 hours. After it was cooled down to room temperature, 5 mL of water was added and the products were extracted by 15 mL of chloroform for three times. After dried by anhydrous MgSO4,the solution was diluted with methanol to 25.00 mL for GC test. The ester products for GC standard curves were synthesized independently following the reported procedures.2
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YieldReaction ConditionsOperation in experiment
75%; 72% With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In water; acetonitrile; at 80℃; for 24h;Sealed tube; General procedure: Under air atmosphere, a sealable reaction tube equipped with a magnetic stir bar and covered with a rubber septum was charged with alcohol compound 1 (1.0 mmol), toluene derivative 2 (4.0 mmol), and Bu4NI (36.9 mg, 10 mol%) in MeCN (2.0 mL). To this mixture was added TBHP (70% wt/v in H2O, 6.0 equiv) at r.t. The rubber septum was then replaced by a Teflon-coated screw cap, and the reaction vessel was placed in an oil bath at 80 C for 24 h. After the completion of the reaction (monitored by TLC), the mixture was cooled to r.t. The resulting solution was poured into a mixture of sat. aq Na2S2O3 (5 mL) and sat. aq NaHCO3 (5 mL), and extracted with EtOAc (2 ×). The combined organic layers were dried (anhyd Na2SO4) and the solvents were removed in vacuo. The residue was purified by flash chromatography on silica gel (eluent: PE/EtOAc) to give the desired product.
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YieldReaction ConditionsOperation in experiment
1: 92% 2: 91% In neat (no solvent) at 20℃; for 2h; General procedure for aroylation of alcohols 2a-i bygrinding with N-aroylbenzotriazoles (1a-d): General procedure: A mixture of N-aroylbenzotriazole 1 (1.0 mmol) and the corresponding alcohol 2 (2.0 mmol) was ground together in a mortar using pestle for the time described in Tables 1 and 2. Completion of the reaction was monitored by TLC in hexane:dichloromethane(1:1) solvent systems. The resulting mixture was purified by preparative thin layer chromatography (silica gel, elution with 50% dichloromethane/hexane) to provide desired ester 3 and benzotriazole (4).
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