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Chemical Structure| 36112-61-5 Chemical Structure| 36112-61-5

Structure of 36112-61-5

Chemical Structure| 36112-61-5

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Product Details of [ 36112-61-5 ]

CAS No. :36112-61-5
Formula : C12H10O3
M.W : 202.21
SMILES Code : O=C(O)C1=C2C=CC(OC)=CC2=CC=C1
MDL No. :MFCD00090331
InChI Key :WRZAWKSSADRYTA-UHFFFAOYSA-N
Pubchem ID :4413708

Safety of [ 36112-61-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 36112-61-5 ]

* 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 [ 36112-61-5 ]

[ 36112-61-5 ] Synthesis Path-Downstream   1~36

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YieldReaction ConditionsOperation in experiment
With aluminum (III) chloride; In chlorobenzene; at 35 - 80℃; for 24h;Catalytic behavior; In a 250ml four-necked bottle, add 20g of furoic acid, 23.2g of anisole, 100ml chlorobenzene, stirred and mixed; oil bath heated to internal temperature 35 ~ 40 C, slowly added 55.9g anhydrous aluminum trichloride; after the completion of the feed, stirring at 75-80 C for about 24 hours; cooling, concentrated distillation under reduced pressure Chlorobenzene After the distillation was completed, the temperature was lowered to room temperature, 60 ml of N,N-dimethylformamide was added to the reaction flask, and the mixture was stirred and mixed. At room temperature, 32.1 g of anhydrous aluminum trichloride was slowly and separately added; after the completion of the feeding, the oil bath was heated to The internal temperature is 135 C, and the reaction is kept for 6 hours; The water is cooled to room temperature; the reaction solution is slowly added to dilute hydrochloric acid solution for hydrolysis; extracted with ethyl acetate several times, and the ethyl acetate extract is combined, washed with water, and Ph is weakly acidic; The organic layer was concentrated under reduced pressure to recover ethyl acetate; The residue is decolorized and recrystallized with dilute alcohol water. Yielding 19.7 g of 6-hydroxy-1-naphthoic acid as a gray to pale yellow powder. Yield: 58.7%, melting point: 205.5 to 208.6 C, purity: 98.5%.
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  • [ 2437-17-4 ]
YieldReaction ConditionsOperation in experiment
19.7 g With aluminum (III) chloride; In N,N-dimethyl-formamide; at 135℃; for 6h; In a 250ml four-necked bottle, add 20g of furoic acid, 23.2g of anisole, 100ml chlorobenzene, stirred and mixed; oil bath heated to internal temperature 35 ~ 40 C, slowly added 55.9g anhydrous aluminum trichloride; after the completion of the feed, stirring at 75-80 C for about 24 hours; cooling, concentrated distillation under reduced pressure Chlorobenzene After the distillation was completed, the temperature was lowered to room temperature, 60 ml of N,N-dimethylformamide was added to the reaction flask, and the mixture was stirred and mixed. At room temperature, 32.1 g of anhydrous aluminum trichloride was slowly and separately added; after the completion of the feeding, the oil bath was heated to The internal temperature is 135 C, and the reaction is kept for 6 hours; The water is cooled to room temperature; the reaction solution is slowly added to dilute hydrochloric acid solution for hydrolysis; extracted with ethyl acetate several times, and the ethyl acetate extract is combined, washed with water, and Ph is weakly acidic; The organic layer was concentrated under reduced pressure to recover ethyl acetate; The residue is decolorized and recrystallized with dilute alcohol water. Yielding 19.7 g of 6-hydroxy-1-naphthoic acid as a gray to pale yellow powder. Yield: 58.7%, melting point: 205.5 to 208.6 C, purity: 98.5%.
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YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; In dichloromethane; at 20℃; for 2h;Heating / reflux; To a solution of 0.18 g (0.90 mmol) of <strong>[36112-61-5]6-methoxy-1-naphthoic acid</strong> (35) in 10 mL of dichloromethane was added dropwise 0.44 ml (5.0 mmol) of oxalyl chloride. The solution was stirred at room temperature for 1 h, then heated at reflux for 1 h. After cooling, the solvent and residual oxalyl chloride were removed in vacuo. The residue was dissolved in 5 mL of toluene and added to a solution of 0.20 g (1.3 mmol) of 1-propylindole in 4 mL of toluene at 0 C. To this solution was added dropwise 0.82 mL (1.5 mmol) of 1.8 M EtAlCl2. The mixture was allowed to warm to ambient temperature and stirred for 18 h. After quenching with water, the reaction mixture was extracted with ether. The ethereal extracts were washed with water, dried (MgSO4) and the solvent was removed in vacuo. The residue was chromatographed (petroleum ether:ethyl acetate, 8:1) to give 0.19 g of JWH-163 as a colorless solid: m.p. 139-140 C.; 1H NMR (300 MHz, CDCl3) delta 0.87 (t, J=7.3 Hz, 3H), 1.81 (sextet, J=7.3 Hz, 2H), 3.91 (s, 3H), 4.01 (t, J=7.2 Hz, 2H), 7.12 (dd, J=9.0, 2.5 Hz, 1H), 7.18 (d, J=2.5 Hz, 1H), 7.30-7.39 (m, 4H), 7.44-7.52 (m, 2H), 7.82 (dd, J=7.5, 1.6 Hz, 1H), 8.09 (d, J=9.0 Hz, 1H), 8.47-8.50 (m, 1H); 13C NMR (75.5 MHz, CDCl3) delta 11.3,23.0,48.7,55.2, 106.0, 110.0, 117.4, 119.3, 122.7, 122.8, 123.5, 123.6, 125.1, 126.1, 126.9, 127.5, 128.7, 135.1, 137.0, 138.0, 139.0, 157.7, 192.1; Anal. Calcd for C23H21NO2: C, 80.44; H, 6.16; N, 4.08; Found: C, 80.30; H, 6.17; N, 3.99.
With thionyl chloride; for 3h;Inert atmosphere; Reflux; Under an argon atmosphere, <strong>[36112-61-5]6-methoxy-1-naphthoic acid</strong> (synthesized by the process of J. D. Moseley and J. P. Gilday, Tetrahedron, 62, 4690-4697 (2006)) (1.20 g, 5.93 mmol) was dissolved in thionyl chloride (5.00 mL, 68.8 mmol) and the solution was heated to reflux for 3 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure to give the crude product of 6-methoxy-1-naphthoyl chloride (22) as a colorless oil.
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YieldReaction ConditionsOperation in experiment
49% In diethyl ether; at 0℃; for 40h;Inert atmosphere; Method E: to a solution of compound 9a (667 mg, 3.30 mmol) inanhydrous Et2O (40 mL) stirred at 0 C under argon was slowlyadded a 1.6 M methyllithium solution (8.26 mL, 13.20 mmol). Theresulting solution was stirred at 0 C for 16 h. After that, two supplementary equivalents of the methyllithium solution were addedand the mixture was stirred at 0 C for additional 24 h. The reactionwas quenched with a saturated ammonium chloride solution andextracted with Et2O. The combined organic layers were dried overMgSO4, filtered, and evaporated under reduced pressure. A purification by silica column chromatography using CH2Cl2 as eluentgave the desired ketone 10a (324 mg, 49%) as an orange oil.1H NMR (300 MHz, CDCl3) d 8.69 (d, 1H, J 9.3 Hz, H8), 7.89 (dd,1H, J 8.4, 1.2 Hz, H2), 7.81 (dd, 1H, J 7.5, 1.2 Hz, H4), 7.46 (dd, 1H,J 8.4, 7.5 Hz, H3), 7.27 (dd, 1H, J 9.3, 2.7 Hz, H7), 7.16 (d, 1H,J 2.7 Hz, H5), 3.93 (s, 3H, CH3O), 2.74 (s, 3H, CH3CO). 13C NMR(75 MHz, CDCl3) d 201.9,157.6,135.5,135.2,131.8,127.6,126.5,125.5,124.9, 120.4, 106.3, 55.2, 29.8.
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YieldReaction ConditionsOperation in experiment
65% To a solution of 0.96 g (3.18 mmol) of 6-methoxy-1-naphthyl trifluoromethanesulfonate in 30 mL of DMF was added 0.034 g (0.15 mmol) of Pd(OAc)2, 0.040 g (0.010 mmol) of 1,3-bis(diphenylphosphino)propane and 1.20 g of triethylamine. The mixture was flushed with carbon monoxide for 25 min, 3.1 mL of 96% formic acid was added dropwise and the reaction was stirred at ambient temperature for 6 h under an atmosphere of CO, diluted with water and extracted with ethyl acetate. The organic extracts were washed with five portions of brine, followed by two portions of aqueous NaHCO3. The bicarbonate extracts were combined, cautiously neutralized with 10% aqueous HCl, and extracted with ether. The ethereal extracts were washed with water, dried (MgSO4) and the solvent was removed in vacuo to give 0.42 g (65%) of acid 35 as a yellow powder. Recrystallization from ethyl acetate:petroleum ether gave pale yellow needles: m.p. 185-186 (lit mp 180-180.5 C., ref. 36); 1H NMR (300 MHz, CDCl3) delta 3.89 (s, 3H), 7.29 (dd, J=6.9, 2.4 Hz, 1H), 7.41 (d, J=2.4 Hz, 1H), 7.53 (t, J=7.8 Hz, 1H), 7.98 (d, J=6.1 Hz, 1H), 8.05 (d, J=8.1 Hz, 1H), 8.79 (d, J=9.1 Hz, 1H); 13C NMR (75.5 MHz, CDCl3) delta 55.2, 106.7, 120.0, 125.4, 126.1, 127.1, 127.5, 127.6, 131.8, 135.2, 157.1, 168.8; MS (EI) m/z 202 (100), 159 (35), 109 (50).
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