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Chemical Structure| 52490-15-0 Chemical Structure| 52490-15-0

Structure of 52490-15-0

Chemical Structure| 52490-15-0

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Product Details of [ 52490-15-0 ]

CAS No. :52490-15-0
Formula : C19H18O3
M.W : 294.34
SMILES Code : O=C(C1=C(CCCC)OC2=CC=CC=C12)C3=CC=C(O)C=C3
MDL No. :MFCD00040947

Safety of [ 52490-15-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P312-P322-P330-P363-P501

Application In Synthesis of [ 52490-15-0 ]

* 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 [ 52490-15-0 ]

[ 52490-15-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 83790-87-8 ]
  • [ 52490-15-0 ]
YieldReaction ConditionsOperation in experiment
100% aluminium chloride; In 1,1-dichloroethane; water; a) 2-n-butyl 3-(4-hydroxy benzoyl) benzofuran To a solution of 2 g (6.5 mmoles) of 2-n-butyl 3-(4-methoxy benzoyl) benzofuran in 30 ml of dichloroethane 1.82 g (13.6 mmoles) of aluminium chloride are added under argon. The mixture is heated at reflux for 9 hours, then cooled to room temperature. The reaction mixture is then poured into 50 ml of water, stirred vigorously for 30 minutes, then the organic phase is separated. It is washed 3 times with 30 ml of water, dried over sodium sulfate and decolorized by means of diatomaceous earth. After evaporation of the solvent, 1.9 g (6.5 mmoles) of 2-n-butyl 3-(4-hydroxy benzoyl) benzofuran are obtained. Yield: 100% M.p.: 119-120 C.
91.6% With aluminum (III) chloride; In chlorobenzene; at 80℃; for 2h;Inert atmosphere; To a solution of compound 3 (1.9 g,5.46 mmol) in chlorobenzene (11 mL) was added AlCl3 (2.2 g, 16.38 mmol).The mixture was stirred at 80 C for 2 hours and was quenched with ice water(20 mL). The reaction mixture was extracted withEA (330 mL). The organicphase was dried over Na2SO4, filtered and concentrated togive the crude product, which was purified by flash chromatography [PE/EA=5:1]to give 4 (1.46g, 78.5%) asa yellow solid. 1H NMR (400 MHz, CDCl3)δ 8.32 (dd, J = 2.4, 0.5 Hz, 1H), 8.22 - 8.18 (m, 1H), 7.79 - 7.75 (m, 2H),7.55 (dd, J = 9.0, 0.5 Hz, 1H), 6.97 - 6.93 (m, 2H), 2.90 (dd, J = 8.1, 7.1 Hz,2H), 1.78 - 1.70 (m, 2H), 1.37 - 1.29 (m, 2H), 0.86 (t, J = 7.3 Hz, 3H).
Ca. 86.9% With aluminum (III) chloride; In toluene; at 80 - 90℃;Large scale; 20.00 kg (64.9 mol, 1.0 eq) of compound 8 was added to 60.00 kg (3 w/w) of toluene.9.52 kg (71.4 mol, 1.1 eq) of aluminum trichloride was added and the reaction was carried out at 80 to 90 C for 2 to 4 hours.After the reaction, the reaction solution was transferred to 90.00 kg (4.5 w/w) of purified water.Adjust the pH to 2 with dilute hydrochloric acid, and wash the organic phase with 50.00 kg (2.5 w/w) of purified water twice.The organic phase was washed with 50.00 kg (2.5 w/w) saturated aqueous sodium chloride solution.It was dried by adding 2.00 kg (0.1 w/w) anhydrous sodium sulfate.The organic phase was concentrated under reduced pressure at 65 C until a solid precipitated, cooled to 0 C, and then allowed to crystallize for 4 hours.Vacuum filtration, wet drying at 80 C,A white crystalline powder of 16.60 kg (56.4 mol) of Compound 9 was obtained in a yield of about 86.9%.
55% With sodium thioethylate; In N,N-dimethyl-formamide; at 110℃; for 16h; In a RBF (100 mL) containing a SB, 86 (400 mg5 1.30 mmol) was diluted with DMF (18.0 mL) and NaSEt (0.426 g, 5.19 mmol) was added. The reaction mixture was heated to 110 C and stirred (16 h). The reaction was quenched by the addition of sat. NH4C1, and was extracted with EtOAc (4 x 25 mL). The combined organic layers were washed with brine, dried (Na2S04), filtered and concentrated in vacuo. The crude material was purified by column chromatography on Si02 (Hex: EtOAc; 4:1) to afford 87 (0.210 mg, 0.713 mmol, 55%) as a light yellow oil. 1H- NMR (400 MHz) CDC13: 7.81-7.78 (d, 2 H), 7.48-7.46 (d, 1 H), 7.37-7.36 (d, 1 H), 7.29-7.25 (m, 1 H), 7.20-7.16 (m, 1 H), 6.94-6.90 (d, 2 H), 6.56 (bs, 1 H), 2.93-2.89 (t, 2 H) 1.79-1.71 (m, 2 H), 1.38-1.32 (m, 2 H), 0.90-0.86 (t, 3 H); 13C-NMR (100 MHz) CDC13: 191.2, 165.0, 160.4, 153.6, 132.1, 131.6, 127.1 , 124.2, 123.4, 121.2, 1 16.7, 1 15.4, 1 1 1.0, 30.1, 27.9, 22.3, 13.7. LC/MS-MS: 295.0 121.2 m/z; GS1 and GS2 at 30, DP = 56, CE = 31 , CXP = 6, tR = 4.51 min.
82.3 g With boron trifluoride diethyl etherate; In acetonitrile; at 80℃; for 2h; 110.9 g (0.36 mol) of 2-butyl-3- (4-methoxybenzoyl) benzofuran obtained in step (1) was charged into a reactor equipped with a magnetic stirrer,Boron trifluoride ether 10.2 g (72 mmol)Soluble in 2L acetonitrile;The mixture was stirred at 80 C for 2 hours,The organic phase is combined and then concentrated under reduced pressure; the recrystallization of ethyl acetate and ether is carried out to obtain the same as that of the ethyl acetate and the ethyl acetate solution,2-butyl-3- (4-hydroxybenzoyl) benzofuran82.3 g (0.28 mol).
8.16 g With aluminum (III) chloride; In toluene; for 6h;Reflux; Add to the 100 ml reaction bottle10.00 g of 2-butyl-(4-methoxybenzoyl)benzofuran,4.50 g of aluminum trichloride and 40 ml of toluene,The temperature was raised to reflux, and the reaction was kept for 6 hours, and the reaction was completed.Cool down to 0 C, pour into ice water, separate the liquid, extract the aqueous phase with toluene, and combine the organic phases.Add an equal volume of water, adjust the pH to above 12 with NaOH solution, and dispense.The aqueous phase is adjusted to pH less than 3 with hydrochloric acid and filtered.The filter cake was dried in vacuo to give a pale yellow solid, 8.16 g.

  • 2
  • [ 52490-15-0 ]
  • [ 81-16-3 ]
  • C29H24N2O6S [ No CAS ]
 

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Technical Information

• Appel Reaction • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Jones Oxidation • Lawesson's Reagent • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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