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[ CAS No. 85-52-9 ]

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2D
Chemical Structure| 85-52-9
Chemical Structure| 85-52-9
Structure of 85-52-9 *Storage: {[proInfo.prStorage]}

Quality Control of [ 85-52-9 ]

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Product Details of [ 85-52-9 ]

CAS No. :85-52-9MDL No. :MFCD00002472
Formula :C14H10O3Boiling Point :257-265°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :226.23Pubchem ID :-
Synonyms :

Computed Properties of [ 85-52-9 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 85-52-9 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 85-52-9 ]

  • Downstream synthetic route of [ 85-52-9 ]

[ 85-52-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 85-52-9 ]
  • [ 18852-53-4 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride;N,N-dimethyl-formamide; In tetrahydrofuran; at 20℃; Dry THF (20 mL) was added to [85-52-9]2-benzoylbenzoic acid (0.51 g, 2.25 mmol) followed by thionyl chloride (0.18 mL, 2.48 mmol) and DMF (3 drops). The reaction mixture was stirred at room temperature overnight and monitored by TLC. Removal of the solvent in vacuo yielded a clear oil (0.55 g, 2.26 mmol, 100%); Rf 0.68 (40:60 ethyl acetate: petrol).
With thionyl chloride; In tetrahydrofuran; benzene; EXAMPLE 1 3-chloro-3-phenyl-1-(3H)-isobenzofuranone Over a period of 15 minutes, 22.5 parts of [85-52-9]2-benzoylbenzoic acid are added, in small portions, while stirring, to 40 parts of thionyl chloride. The reaction mixture is then brought slowly to reflux and this is maintained for 90 minutes. The excess thionyl chloride is removed in vacuo and the residue is taken up in 50 parts of anhydrous benzene and the whole is then evaporated to dryness in vacuo. The operation is repeated a second time and then the residue is taken up in 80 parts of anhydrous tetrahydrofuran. This solution is used in that form in the stage described below.
With thionyl chloride; N-benzyl-N,N,N-triethylammonium chloride; at 50℃; for 4.5h;Catalytic behavior; 132 g of thionyl chloride and 226 g of o-benzoylbenzoic acid were placed in a 1000 ml four-neck reaction flask, stirred well, and then cast.After adding 0.68 g of benzyltriethylammonium chloride, the temperature was raised to 50 C, and after 4.5 h of incubation, the TLC tracking showed that the starting point disappeared.Should be completed, down to normal temperature, add 340g of trichloroacetaldehyde, 11.3g of concentrated hydrochloric acid and 0.25g of sulfamic acid, began to heat up to 90After C for 2h, TLC tracking showed that the raw material disappeared, the reaction was finished, and it was reduced to normal temperature. 5% liquid alkali was added dropwise to adjust the system.pH, wait until the pH value is about 7, and let stand and separate the water layer. Start rectification and recovery of trichloroacetaldehyde (97.5-99 C), recovery rate of 90%, recyclingAfter completion, continue to heat up and recover the middle distillate. The middle distillate includes trichloroacetaldehyde, water and a small amount of finished product (112~130 C). ContinueThe temperature is recovered from the fraction between 157.1 and 165 C, and the fraction is the finished 2-(benzoyl)benzoyl chloride, the yield is 95.4%, pure99.7%, the residual value after rectification of the product is a small amount of yellow viscous residual liquid and waste residue, which is poured out hot and concentrated.
  • 2
  • [ 85-52-9 ]
  • [ 5004-45-5 ]
YieldReaction ConditionsOperation in experiment
99% With carbazic acid; at 90℃; for 3h;Green chemistry; General procedure: A 10.0 mmol for alpha-keto acid compound or a 5.2 mmol for beta-diketones or alpha-keto acids was mixed with 0.40 g of hydrazinium carboxylate (1a, 5.2 mmol), respectively. (For solid di-carbonyl compound, the mixture was ground using a pestle and a mortar.) The mixture was stored in a closed vial, and then heated to 70 - 90 C until the reaction was complete. Complete conversion to related product was dependent upon the nature of di-carbonyl compounds. Typically, those di-carbonyl compounds take about <3 h to complete the reactions. CO2 and water were released during the reaction. All products obtained from the reactions of 1a with di-carbonyl compounds were basically characterized by 1H and 13C NMR spectroscopy. The products have over 97% of purity of reaction mixture based on 1H NMR spectroscopy and isolation yields are over 97% based on di-carbonyl compounds. The melting points, elemental analysis and UV-Vis spectra for all azines, pyrazoles and pyridazinones, were measured after purification using appropriate solvent.
89% With hydrazine hydrate; In ethanol; for 6h;Reflux; [85-52-9]2-benzoylbenzoic acid (5.66 g, 25 mmol) and 2 mL of 85% hydrazine hydrate were placed in a 150 mL round bottom flask, and then 50 mL of ethanol was added thereto and heated under reflux for 6 h. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered under reduced pressure. The solid was washed three times with a small amount of a mixed solvent of ethanol and water, and dried at 60 C for 24 hours to give 4-phenyl-1,2-dihydrophthalazine-1-one as a white solid 4.94 g, yield 89%.
72% With sodium hydroxide; hydrazinium sulfate; In water; for 1h;Reflux; General procedure: A solution of hydrazine sulfate (4.0 g, 30.4 mmol) and sodium hydroxide (2.4 g, 60.8 mmol) in water (20 mL) was heated on a steam bath for 20 min, then the latter was added to solution of 8a, b (30.4 mmol) in water (20 mL). The reaction mixture was heated under reflux for 1 h, upon cooling the residue obtained was filtered, washed with water and crystallized from propanol to obtain the desired compounds 9a, b, respectively [32].
With hydrazine hydrate; In ethanol; for 3h;Reflux; General procedure: 2-Acetyl or [85-52-9]2-benzoylbenzoic acid derivatives (0.01 mol) and hydrazine hydrate (0.01 mol) in 30 mL of ethanol were refluxed for 3 hours. At the end of this period, the reaction mixture was cooled and the resulting precipitate was filtered to give compounds 2 and 3 respectively.

  • 3
  • [ 85-52-9 ]
  • [ 5398-11-8 ]
YieldReaction ConditionsOperation in experiment
66% General procedure: Method B:22 NaBH4 (227 mg, 6.00 mmol) was added at 0 C to a solution of NaOH (500 mg, 12.5 mmol) and the corresponding keto acid (5mmol) in H2O (10 mL). The reaction mixture was stirred at r.t. for more than 2 h. After completion of the reaction, concd HCl was carefully added until the pH of the resultant solution reached 2. The solution was then extracted with CH2Cl2 (3 × 15 mL), and the organic phases were combined, dried (anhyd Na2SO4), and evaporated under reduced pressure. The resultant oil or solid was directly dissolved in CH2Cl2 (18 mL) with trifluoroacetic acid (0.75 mL) and the solution was stirred at r.t. for more than 24 h. Afterwards, the solution was cooled and washed with sat. aq Na2CO3 (15 mL). Then, the solution was extracted with CH2Cl2 (3 × 15mL), and the organic phases were combined, dried (anhyd Na2SO4) and evaporated under reduced pressure. The crude product was purified by a bulb-to-bulb distillation to give the corresponding lactone.
  • 4
  • [ 85-52-9 ]
  • [ 685-87-0 ]
  • [ 37617-98-4 ]
YieldReaction ConditionsOperation in experiment
84% 5.1.2 PREPARATION OF 4-PHENYL-3-ISOCOUMARINCARBOXYLIC ACID (102): Following a literature procedure (Natsugary et al, J. Med. Chem. 1995, 38, 3106-3120), Compound 102 was synthesised. A suspension of 2-benzoyl-benzoic acid (33.9 g, 0.15 mol), anhydrous potassium carbonate (41.4 gm, 0.3 mol) and diethyl bromomalonate ((28.17 mL, 0.165 mol) in DMF (250 mL) was allowed to stir overnight at room temperature. The reaction mixture was then poured on cold water, and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated. The residue obtained was treated with acetic acid (1.0 L), followed by concentrated HCl (800 mL), and then refluxed for 6 hours. The reaction mixture was cooled to room temperature and poured on ice cold water, and the precipitate that formed was filtered, washed thoroughly with water, and dried to provide 32.6 g of Compound 102, a white solid, in 84% yield.
84% 5-123a) Preparation of 4-Phenyl-3-isocoumarincarboxylic acid (3a) Following the procedure described in Natsugary et al., J. Med. Chem. 38, 3106-3120 (1995), compound 3a (Scheme 1-123) was synthesised. A suspension of 1a (33.9 g, 0.15 mol) (Scheme 1-123), potassium carbonate (41.4 g, 0.3 mol) and diethyl bromomalonate (28.17 mL, 0.165 mol) in DMF (250 mL) was stirred at room temperature for 15 h. The reaction mixture was then diluted using cold water and extracted into ethyl acetate. The ethyl acetate layer was dried over sodium sulfate, and concentrated in vacuo to afford a crude residue to which was added glacial acetic acid (1.0 L) and concentrated HCl (800 mL). The resulting solution was heated at reflux for 6 h. The reaction mixture was cooled to room temperature and poured on ice water. The solid precipitate was filtered, washed with water and dried using vacuum to provide compound 3a as a white solid. Yield=32.6 g (84%).
84% Following a known procedure (Natsugary et al, J. Med. Chem. 1995, 38, 3106 - 3120), Compound 102-145 was synthesized. A suspension of 2-benzoyl-benzoic acid (33.9 g, 0.15 mol), anhydrous potassium carbonate (41.4 gm, 0.3 mol) and diethyl bromomalonate ((28.17 mL, 0.165 mol) in DMF (250 mL) was allowed to stir overnight at room temperature. The reaction mixture was then poured on cold water, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. The residue obtained was treated with acetic acid (1.0 L), followed by concentrated HCl (800 mL), and then refluxed for 6 hours. The reaction mixture was cooled to room temperature and poured on ice cold water, and the precipitate that formed was filtered, washed thoroughly with water, and dried to provide 32.6 g of Compound 102-145, a white solid, in 84% yield.
  • 5
  • [ 85-52-9 ]
  • [ 22103-85-1 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; In dichloromethane; at 20 - 38℃; for 20h; A four-necked round-bottom flask equipped with a mechanical stirrer, thermocouple, dropping funnel and condenser is charged successively with 100 g of 2-benzoyl-benzoic acid and 300 ml of dichloromethane. The mixture is cooled to 20 0C and 164 g of thionyl chloride are dropped to the solution. The reaction is heated at 38 0C for 20 hours and then concentrated under reduced pressure. 2-benzoyl-benzoyl chloride is obtained as white solid with a melting point of 66-73 0C. The proposed structure is confirmed by NMR analysis
With thionyl chloride; at 50℃; Methyl l-oxo-3-phenyl-lH-indene-2-carboxylate was prepared by reference to the procedure of Barvian, M. R. et al., Bioorg. Med. Chem. Lett., 1997,22, 2903-2908, and the procedure of Yost, W. L. and Burger, A., J. Org. Chem., 1950, 15, 1113-1118.[85-52-9]2-Benzoylbenzoic acid (3.09 g, 13.7 mmol) was dissolved in SOC12 (15 mL) and heated at 50 C overnight (ca. 18 hours). The SOC12 was removed in vacuo (coevaporated with tetrahydrofuran) to afford the acid chloride, an amber oil, which was immediately carried through to the next step. Dimethyl malonate (1.99 g, 15.0 mmol) in tetrahydrofuran (20 mL) was added to a solution of potassium tert-butoxide (1.69 g, 15.0 mmol) in tetrahydrofuran (80 mL) and the mixture was stirred for 20 minutes. The acid chloride in tetrahydrofuran (30 mL) was added and the mixture was refluxed for 3 hours and then allowed to cool to room temperature overnight (ca. 15 hours). The solvent was removed in vacuo to afford an amber oil which was dissolved in Et2O (200 mL) and washed with 5% HCl (3 x 200 mL). The solvent was removed in vacuo to afford an amber oil, which was suspended in 10% sodium carbonate solution (70 mL). This solution was heated (50 C) until it turned clear (1.5 hours). A dark yellow oil appeared in the bottom of the flask and was collected with the aid of a separatory funnel. The solution was then neutralized by the addition of 6 M HCl and a dark yellow precipitate formed which was collected with the aid of a Buchner funnel. The oil and solid were purified separately by silica flash column chromatography (1: 9 EtOAc/hexane) to afford compound (1) as a dark yellow solid (combined yield: 246 mg, 7%), m. p. 89-92 C (no lit. m. p.). Rf 0. 21 (1: 4 EtOAc/hexane). EI-MS: 264 (M) +, 233 (M-OCH3) +, 176, 88.'H NMR (500 MHz, CDC13) 8 7.61 (m, 1H, Ar-H); 7.53 (m, 5H, 5Ar-H) ; 7.42 (m, 2H, 2Ar-H); 7.20 (m, 1H, Ar- H); 3.75 (s, 3H, COOCH3)."C NMR (125 MHz, CDCl3) 8 192.0, 165.6, 163.4, 143.1, 133.5, 131.4, 131.1, 130.5, 130.5, 128.5, 128.1, 124.0, 123.5, 123.5, 51.8. HRMS (EI) calcd for Cl7Hl203 264.0786, found 264.0786.
With thionyl chloride;N,N-dimethyl-formamide; In tetrahydrofuran; at 20℃; for 16h; To a solution of the appropriate [85-52-9]2-benzoylbenzoic acid (1.0 equiv.) in THF was added thionyl chloride (2.2 equiv.) and DMF (3 drops). The mixture was stirred at room temperature 16 h, then concentrated in vacuo to give a clear oil. The residues were dissolved in THF (10 mL), the appropriate primary amine (1.0 equiv.), and triethylamine (2.2 equiv.) were added, and the mixture stirred at rt for 16 h. The mixture was either filtered and submitted to extraction with EtOAc (15 mL), sodium bicarbonate (20 mL) and water (15 mL) or treated immediately with EtOAc (15 mL), saturated sodium bicarbonate (15 mL) and water (15 mL). The organic layers were combined, dried (Na2SO4) and concentrated in vacuo. Chromatography (EtOAc, petrol 1 :4) or by crystallisation with a minimum of EtOAc and an excess of petrol gave the desired product.; 2-benzoyl benzoic acid (0.75 g, 3.3 mmol), 2-aminoethyl methacrylate hydrochloride (0.60 g, 3.65 mmol), and triethylamine (1.01 mL, 7.26 mmol) in THF (10 mL. Chromatography (silica; EtOAc, petrol; 3: 7) gave 1Od as a clear oil (1.04 g, 3.08 mmol) FTIR v (cm4): 3326 (OH), 2930 (CH-Ar), 1679 (very strong C=O absorption). 1H NMR (300 MHz' CDCV deltaH (ppm) 1.90 (3H, s, CH3), 3.13 (1Eta, m, CH2), 4.12 (2Eta, m, OCH2), 4.67 (1Eta, m, NCH2), 5.58 (1Eta, s, CH), 6.09 (1Eta, s, CH), 7.28-7.80 (13Eta, m, Ar-H), 7.81 (IH, m, Ar-H4). ?3C NMR (75 MHz, CDcn deltaC (Ppm) u 6 (CH3), 18.7 (CH2), 38.9 (CH2), 63.5 (CH2), 91.8 (O-C-N), 123 -149.5 (C-Ar), 168.3 (C=O), 168.5 (C=O). LCMS (ESI+) m/z = 360, [M+Na]+.
With thionyl chloride;N,N-dimethyl-formamide; In dichloromethane; for 4h; A mixture of [85-52-9]2-benzoylbenzoic acid (3.88 g, 16.7 mmol) in CH2Cl2 (15 mL), SOCl2 (6.0 mL, 82 mmol), DMF (0.13 mL, 1.7 mmol) was stirred under N2 atmosphere for 4 hours. The thionyl chloride excess was removed by azeotropic distillation with toluene under reduced pressure to yield the correspondent acyl chloride as brown oil. To a mixture of magnesium turnings (0.40 g, 16.7 mmol) in absolute ethanol (0.50 mL), and CCU (0.10 mL) was added freshly distilled diethyl ether (10 mL). After stirring at room temperature for 10 min, a solution of diethyl malonate (2.5 mL, 16.5 mmol) in freshly distilled diethyl ether (10 mL) and absolute ethanol (2 mL) was added dropwise. The resulting mixture was refluxed under for 3 h and, after this time, a solution of the acyl chloride in diethyl ether (15 mL) was added. The reaction mixture was refluxed for 30 min, cooled to 0-5 0C, and acidified with 10% H2SO4. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to yield a brown oil. A mixture of this residue in ethanol (80 mL) and water (30 mL) with Na2CO3 (4.0 g, 38 mmol) was refluxed for 20 minutes, then concentrated under reduced pressure, diluted with water, acidified with IN HCl, and extracted with CH2Cl2. The organic layer was washed with a diluted solution of NaHCO3, dried over sodium sulfate, and evaporated under reduced pressure. The residue was purified by crystallization from diethyl ether at - 18 0C to give indenone Ii as yellow crystalline solid (2.9 g, yield 62 %, mp 85-87 0C, literature15 88-89 0C). 1H-NMR (200 MHz, CDCl3): 1.16 (t, J = 7.1, 3H), 4.20 (q, J = 7.2, 2H), 7.20 (m, IH), 7.38-7.53 (m, 7H), 7.59 (m, IH).
With thionyl chloride; for 2h;Reflux; 2-Benzoyl-benzoyl chloride was formed by the addition of SOCl2 (5 mL) to 2-benzoyl-benzoic acid (565 mg, 2.5 mmol) and stirring under reflux for 2 h. Excess of SOCl2 was removed under reduced pressure and the crude material was used in the next step without purification. To a solution of 2-benzoyl-benzoyl chloride (70 mg, 0.29 mmol) in anhydrous DCM (1mL) was added respectively rac-1 (50.0 mg, 0.136 mmol), Et3N (80 muL, 0.57 mmol) and DMAP (7 mg, 0.057 mmol). The mixture was stirred at rt for 2 h and poured over ice bath. After extraction with AcOEt (25 mL), the organic layer was washed with brine (10 mL), dried over MgSO4 and evaporated under reduced pressure. The crude material was purified by preparative TLC (15% of MeOH in CHCl3) to give two solid compounds. Each product was dissolved in AcOEt (50 mL), washed with 1M HCl solution (10 mL) and dried over MgSO4. The organic solutions were concentrated under reduced pressure to afford 6 (10 mg, 0.017 mmol, 13%) and 7[15] (17 mg, 0.049 mmol, 36%), both as white solids.
59 g With thionyl chloride; for 1h;Reflux; To a 500 mL round bottom flask was added o-benzoylbenzoic acid (50 g, 221 mmol (millimoles)),Then add 150mL thionyl chloride dissolved,Heat to reflux for 1 hour (TLC tracking).After the reaction was completed, the thionyl chloride was evaporated to dryness under reduced pressure at 60 C, Get 592g of brownish-yellow oily substance, without further purification, directly cast one step.

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