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[ CAS No. 99-93-4 ] {[proInfo.proName]}

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Chemical Structure| 99-93-4
Chemical Structure| 99-93-4
Structure of 99-93-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 99-93-4 ]

CAS No. :99-93-4 MDL No. :
Formula : C8H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :TXFPEBPIARQUIG-UHFFFAOYSA-N
M.W : 136.15 Pubchem ID :7469
Synonyms :
P-hydroxyacetophenone

Calculated chemistry of [ 99-93-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.66
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : 1.35
Log Po/w (WLOGP) : 1.59
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.68
Consensus Log Po/w : 1.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.91
Solubility : 1.66 mg/ml ; 0.0122 mol/l
Class : Very soluble
Log S (Ali) : -1.74
Solubility : 2.5 mg/ml ; 0.0184 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.13
Solubility : 1.02 mg/ml ; 0.00746 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 99-93-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 99-93-4 ]

* 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 [ 99-93-4 ]

[ 99-93-4 ] Synthesis Path-Downstream   1~85

  • 1
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  • [ 99-93-4 ]
  • 2
  • [ 100-52-7 ]
  • [ 99-93-4 ]
  • [ 2657-25-2 ]
YieldReaction ConditionsOperation in experiment
95% In neat (no solvent); at 50℃; for 0.416667h;Milling; Green chemistry; General procedure: To a mixture of ketone (1 mmol) and aldehyde (2 mmol for Table 2; 1 mmol for Table 3), Mo10V2/SiO2 (produced 40 wt.%: of Mo10V2 to silica19, 32.5wt.% from ICP result, typically, the Mo content from ICP was slightly lower than expected from the preparation stoichiometry) (0.06 g, 0.085 mol% ofMo10V2 to ketone as substrate) was added and crushed at 50 C for appropriatetime. Completion of the reaction was monitored by TLC, using n- hexane/ethylacetate (10:4) as eluent. After completion of the reaction, 2×10 mL of ether was added to the mixture and filtered off. Catalyst was washed withether and dried for reusing. The solvent of the filtrate was evaporated then followed by chromatography to obtained pure products.
93.9% With potassium hydroxide; In ethanol; at 20℃; General procedure: As outlined in Figure 2, an aqueous solution of KOH (20% w/v,2 mL) was added to a stirred solution of the appropriate acetophenone(1 mmol, 1 equiv) in ethanol (2 mL). The mixture was stirredat room temperature for 10 min. After complete dissolution, arylaldehyde (1 mmol, 1 equiv) was added slowly and the reactionmixture was then stirred at room temperature for 24-72 h. Aftercompletion, the mixture was cooled to 0 C on an ice bath and acidifiedwith HCl (10% v/v aqueous solution). In most cases, the productsprecipitated out upon acidification with HCl. The crudeproduct was filtered and further purified by recrystallization fromethanol. In the cases in which no precipitate formed, the mixturewas extracted with ethyl acetate and washed with brine and water.After drying over Na2SO4, the solvent was removed by rotary evaporationto give the crude product which was further purified byeither recrystallization or automated medium performance liquidchromatography, eluting with an ethyl acetate/hexanes gradient(0-60%).
90% With nitrogen doped BaO/fly ash; for 0.0333333h;Microwave irradiation; General procedure: Microwave irradiation method: An appropriate equimolar quantity of substituted 4-chlorobenzaldehyde (2 mmol), acetophenone (2 mmol) and fly ash based catalyst (0.75 g) have been taken in borosil tube and tightly capped. The mixture is exposed to microwave for 2-3 min in a microwave oven and then cooled at room temperature. The organic layer has been separated with dichloromethane which on evaporation yielded the solid product. The solid on recrystallization with benzene-hexane mixture gives glittering solid. The insoluble catalyst has been recycled by washing the solid reagent remained on the filter by ethyl acetate followed by drying in an oven at 100 C for 1 h. This recycled catalyst has been made reusable for further reactions.
88% With silica-gel-supported sulfuric acid; In neat (no solvent); at 65℃; for 1.5h; General procedure: The SSA (0.02 g) was added to a well stirred suspension of PhAc (1 mL, 0.90 g, 7.53 mmol, 1 eq.) and PhCHO (0.84 g, 7.91 mmol, 1.05 eq.) and the resulting mixture was heated at 65 C for 1.5 h. The reaction mixture was cooled to room temperature and partitioned between brine (25 mL) and CH2Cl2 (3 × 15 mL) and solid SSA was filtered off. The SSA was washed with acetone (25 mL) to ensure desorption of product on SSA surface. The combined organic extract was washed with brine (3 × 25 mL) and the organic extract was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the chalcone as colorless solid (1.48 g, 91%).
85.3% With sodium hydroxide; In ethanol; water; at 20℃; for 24h; A mixture of 4-hydroxyacetophenone (1.36 g, 10 mmol), benzaldehyde(1.3 mL, 11 mmol) and sodium hydroxide (1 g, 25 mmol)were dissolved in ethanol/water (4:1 v/v, 20 mL) and stirred atroom temperature for a period of 24 h. 10% HCl was added toadjust the solution to pH = 3 and the product precipitated. Filtrationof the reaction mixture gave a light yellow solid product witha yield of 85.3%.
78% With potassium hydroxide; In ethanol; water; at 20℃; General procedure: The commercially available hydroxyacetophenone (1.0 mmol) was dissolved inethanol (10ml) with 20% aqueous potassium hydroxide solution (1ml), then theappropriate benzaldehyde (1.0 mmol) was added drop by drop to the mixture. Thesolution was stirred at room temperature for 6-12 h to prepare compounds 1-7. Thepiperidine (0.5 ml) was used as a catalyst at 80 C to obtain compounds 8-15.Compounds 16-18 were synthesized via the condensation of the hydroxyl-protectedstarting materials and deprotected subsequently. The reaction progress was monitoredusing silica gel TLC with Petroleum ether/EtOAc as mobile phase. Upon completion,the mixture was poured into water and adjusted to pH 5, which was extracted with 3 × 30 mL of EtOAc, washed with brine, dried over anhydrous Na2SO4 and purified bychromatography (PE/EA) on silica gel.
74% With potassium hydroxide; In ethanol; water; at 20℃;Sonication; General procedure: A modied Claisen-Schmidt condensation was performed between 4-hydroxy acetophenone and the suitable substituted aryl aldehyde at a molar ratio 1:1 in absolute ethanol (10 mL) [29]. Three milliliters (3 mL) aqueous KOH (20%) was added. The mixture was stirred at room temperature in a US-bath. The end of the reaction was monitored by TLC. The mixture was treated with aqueous HCl 10% and adjusted to acidic pH. The precipitate was either ltered and washed with cold water or extracted with CHCl3 (30 mL × 3). The combined organic layers were washed with water and brine and dried under anhydrous MgSO4. The product was evaporated to dryness and puried by recrystallization from a proper solvent.
72% With sodium hydroxide; In ethanol; for 0.12h;Cooling with ice; 4-(hydroxyacetophenone (4.0g),Benzaldehyde (4.0 g) and 100 mL of ethanol were added to a 500 mL three-necked flask and stirred for about 30 minutes.24 mL of 4 mol/L NaOH solution was added to the system, and after the dropwise addition was completed, the mixture was stirred in an ice bath for about 12 hours. After the reaction is over,Transfer the system to a 500 mL beaker and add the appropriate amount of ice water.Then, after adjusting the pH of the system to about 5-6 with a 5% dilute hydrochloric acid solution,A large amount of milky white solid precipitated and the solid was withdrawn in a yield of 72%.
71% With potassium hydroxide; In ethanol; at 5 - 20℃; for 4h; A mixture of phydroxyacetophenone(4.9 mmol) and benzaldehyde (4.9mmol) in EtOH (7.5 mL) was stirred at 5 C for 10 m. Then,a solution of KOH 40% (34.4 mmol) was added and the reactionmixture was stirred at room temperature for 4 h. Themixture was acidified with HCl 2N until pH 7 was reached.When the chalcone precipitated, it was filtered, washed withwater and dried under reduced pressure. Yellow solid, 71%yield, m.p. 172-174 C. IR (KBr) 3239, 1646 cm-1; 1H NMR(CD3OD) 6.70 (d, 2H, J = 9.0 Hz, CH Ar), 7.41-7.43 (m,3H, CH Ar and HC=CH), 7.71-7.75 (m, 4H, CH Ar andHC=CH), 8.02 (d, 2H, J = 9.0 Hz, CH Ar); 13C NMR(CD3OD) 115.29 (CH Ar), 121.71 (=CHC=O), 128.43 and128.86 (CH Ar), 129.67 (O=CCAr), 130.35, 131.25 and 135.27 (CH Ar), 143.90 (C Ar),143.95 (ArCH=), 162.87(CArO), 189.49 (ArC=O).
70% With water; sodium hydroxide; In ethanol; at 5 - 25℃;Inert atmosphere; General procedure: An aqueous solution of NaOH (20%, 5mL) was added dropwise to a previously cooled mixture of selected acetophenone (5mmol) and selected (hetero)aryl aldehydes (5mmol) in EtOH (25mL) under vigorous stirring. The mixture was stirred at RT for 24-72h. After completion of the reaction (as indicated by TLC), the mixture was poured onto crushed ice and acidified with dilute HCl. The precipitated product was filtered at suction and washed to neutral filtrate. The solid was recrystallized from EtOH to get crystalline product.
69% With sodium hydroxide; In ethanol; at 20℃; Add 100 mL flask to join three-hydroxyacetophenone (2.72g, 20 mmol) and benzaldehyde (2.12g, 20mmol) added, and 20 mL of absolute ethanol, with stirring, the solid was dissolved, the reaction system as a pale yellow transparent liquid, to which was added dropwise 20% sodium hydroxide solution 6ml, reddish-brown liquid reaction system.Stirring at room temperature, TLC tracking progress of the reaction, after the disappearance of raw materials point to stop the reaction, the reaction system was poured into ice water with dilute hydrochloric PH = 6-7, a yellow solid precipitated, filtration and drying to give a crude product, the crude product was free water was recrystallized from ethanol to give a yellow solid, mass 3.10 g (theory 4.49 g of the mass), yield 69%.
67% With sodium hydroxide; In water; at 20℃; General procedure: Toa stirred solution of acetophenone derivatives (1 mmol) and a benzlaldehydederivatives (1 mmol) in EtOH (10mL) was added 10%NaOH (4 mL) and the reaction mixturewas stirred for 12-24 h until the solids formed. The reaction was monitored byTLC. When the reaction completed, themixture was poured into an excessive amount of ice water. Then the products were filtrated and washed carefully with ice water and cold EtOH; the resulting chalcones were purified by crystallization from EtOH in refrigerator to givethe title compounds. (Scheme 1)
65% With lithium hydroxide monohydrate; In ethanol; at 20℃; for 2.25h; General procedure: To an ethanol solution of the substituted acetophenones(1.0 equiv) was added LiOHH2O (1.0 equiv). The reaction mixture was stirred for 15 min at room temperature and then treated withthe desired benzaldehyde (1.2 equiv). The mixture was stirred for2 h at room temperature. The reaction mixture was quenched withH2O (100 mL) and then diluted with EtOAc (200 mL) and washedwith H2O (2 200 mL) and brine (200 mL). The organic layer wasdried with anhydrous Na2SO4 and concentrated in vacuo. The residuewas purified by column chromatography on SiO2
With sodium hydroxide; In ethanol; at 20℃; for 12h; General procedure: Intermediates a1-a13 were synthesized by the aromatic aldehydes with p-hydroxyacetophenone in the presence of NaOH in ethanol for 12 h at room temperature.1 Intermediate 3-(chloromethyl)quinazolin-4(3H)-one d was synthesized from 2-aminobenzoic acid in three steps including cyclization, addition, and chlorination reaction,2 In addition, a mixture of 3-chloromethyl-4(3H)-quinazolinone d (1.0 mmol), (E)-1-(4-hydroxyphenyl)-3-arylprop-2-en-1-one a1-a13 (1.0 mmol), K2CO3 (1.2 mmol) were dissolved in CH3CN (30 mL). After refluxing for 3-5 h, cooling and filtering, the intermediates e1-e13 were recrystallized from ethanol to obtain. The structures of the intermediates e1-e13 were confirmed on the basis of IR, 1H NMR and 13C NMR.
With sodium hydroxide; In methanol; at 20℃; for 0.833333h; General procedure: Chalcones were synthesized according to the previously described methodology29. A substituted acetophenone (5 mmol) and benzaldehyde(5 mmol) were dissolved in dry methanol (30 ml). To this methanolic solution, 5ml of sodium hydroxide (50%) was slowly added. Stirring was continued (20 min.-1 h) at room temperature and to neutralize the contents, 1N HCl was added. Reaction time taken for the completion of reactions is mentioned in Table.1. A mixture of ethyl alcohol and water was used for recrystallization. The synthetic procedure and reaction conditions for chalcones are illustrated in scheme 1.
With sodium hydroxide; In ethanol; at 20 - 25℃; for 3h; General procedure: An equimolar mixture of 4-hydroxyacetophenone (1) and substituted benzaldehydes (2a-b) in ethanol stirred magnetically, NaOH solution (10%) was added drop wise to the reaction mixture with vigorous stirring maintaining temperature 20-25C. The reaction mixture was further stirred for 3 h, cooled, and refrigerated overnight. The crude chalcones (3a-b) were filtered, dried, and recrystallized using rectified spirit.

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  • 3
  • [ 50-00-0 ]
  • [ 6091-44-7 ]
  • [ 99-93-4 ]
  • [ 42528-76-7 ]
  • 4
  • [ 60632-40-8 ]
  • [ 99-93-4 ]
  • 6-bromo-4.4'-dihydroxy-3-methoxy-<i>trans</i>(?)-chalcone [ No CAS ]
  • 5
  • [ 99-93-4 ]
  • [ 6322-56-1 ]
YieldReaction ConditionsOperation in experiment
91% With yttrium(lll) nitrate hexahydrate; In acetic acid; at 20℃; for 4h; Phenol (94 mg, 1 mmol) dissolved in 3 mL glacial acetic acidin a 50 mL test tube was treated with solid Y(NO3)3.6H2O(383 mg, 1 mmol) with constant shaking at RT for 10 min.The reaction was monitored by TLC at 10% EtOAc inPetroleum benzene. Ice-cold water (30 mL) was added to thereaction mixture after completion of reaction and left for 15min. Solid was collected by filtration and washed with water.Solid product isolated in this way was used for analysis withoutfurther purification. Experimental procedure for the synthesisof compounds 2a-2e is mentioned in the SupportingInformation.
79.8% With nitric acid; In sulfuric acid; STR84 5.00 g (36.7 m mole) of 4-acetylphenol was dissolved in 50 ml of sulfuric acid. To the mixture solution 3.10 ml (40.7 m mole) of nitric acid (60%, d=1.38) was gradually added dropwise, keeping the reaction temperature at 2-10 C. and cooling with ice under stirring. Then the mixture solution was stirred at the same temperature. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was filtered, washed with water and recrystallized from methanol to obtain 5.84 g of 2-nitro-4-acetylphenol (Yield: 79.8%).
79.8% With nitric acid; In sulfuric acid; EXAMPLE 5 2-(4-decyloxyphenyl)-5-octyloxybenzoxazole (Example Compound No. 1-114) was synthesised through the following reaction schemes. STR81 5.00 g (36.7 ml) of 4-acetylphenol was dissolved in 50 ml of sulfuric acid. To the solution, 3.10 ml (40.7 mM) of nitric acid (60%, density=1.38) was gradually added dropwise under stirring at 2-10 C. on an ice bath, followed by stirring at 2-10 C. after the addition. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by recrystallization from methanol to obtain 5.84 g of 2-nitro-4-acetylphenol (Yield: 79.8%).
65% With sodium nitrate; potassium hydrogensulfate; silica gel; In dichloromethane; at 20℃; for 12h; General procedure: To a solution of 4-hydroxybenzophenone or 4-hydroxyacetophenone (1.26 mmol) in dichloromethane(15 mL), potassium hydrogen sulfate (6.82 mmol), sodiumnitrate (7.32 mmol), and 0.875 g of wet silica 50% p/p wasadded. The slurry was was left under constant stirring atroom temperature until the completion of the reaction,checked by TLC (hexane/ethyl acetate, 8:2v/v). Then themixture was filtered through silica, the solid was washedwith dichloromethane and the solvent removed underreduced pressure. The products were then purified byrecrystallization.

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  • 6
  • [ 20098-48-0 ]
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  • 8
  • [ 81196-09-0 ]
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  • (4-tert-Butoxycarbonylamino-phenyl)-acetic acid 4-acetyl-phenyl ester [ No CAS ]
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  • [ 102123-74-0 ]
  • [ 99-93-4 ]
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  • [ 99-93-4 ]
  • [ 2491-38-5 ]
  • [ 1836-06-2 ]
  • 11
  • [ 2921-14-4 ]
  • [ 99-93-4 ]
  • [1-(4-Hydroxy-phenyl)-eth-(E)-ylideneaminooxy]-acetic acid [ No CAS ]
  • 12
  • [ 6429-10-3 ]
  • [ 99-93-4 ]
  • 4-[2-(4-Acetylphenoxy)ethyl]-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium iodide; oxalic acid; potassium carbonate; In N-methyl-acetamide; isopropyl alcohol; EXAMPLE 113 4-[2-(4-Acetylphenoxy)ethyl]-1H-imidazole 816 mg (6 mmol) of 4-hydroxyacetophenone, 251 mg (1.5 mmol) of 4-[2-chloroethyl]-1H-imidazole hydrochloride, 500 mg (3.6 mmol) of potassium carbonate and sodium iodide (catalyst) are stirred at 80 C. for 5 days in 5 ml of dimethylformamide. The reaction mixture is cooled, filtered and the filtrate is evaporated under reduced pressure to give an oily residue, from which 4-hydroxyacetophenone is extracted with ether at pH=1. Subsequent extraction with ethyl acetate at pH=9 gives the title compound. The latter was treated with oxalic acid in 2-propanol to give the oxalate of the title compound which is crystallized from a methanol/ether (10/1) mixture, M.p.: 178-182 C.
  • 13
  • [ 105-56-6 ]
  • [ 17028-61-4 ]
  • [ 99-93-4 ]
  • 4-amino-2-(4-hydroxy-phenyl)-7-methoxy-9-nitro-chromeno[3,4-<i>c</i>]pyridin-5-one [ No CAS ]
  • 14
  • [ 99-93-4 ]
  • [ 1197-09-7 ]
  • [ 6322-56-1 ]
  • 15
  • [ 529-53-3 ]
  • KOH-solution [ No CAS ]
  • [ 99-93-4 ]
  • [ 99-96-7 ]
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  • [ 2657-25-2 ]
  • aqueous KOH [ No CAS ]
  • [ 100-52-7 ]
  • [ 99-93-4 ]
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  • [ 3747-74-8 ]
  • [ 99-93-4 ]
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  • [ 99-93-4 ]
  • [ 403-14-5 ]
  • [ 133186-55-7 ]
  • 20
  • [ 454-73-9 ]
  • [ 99-93-4 ]
  • 4'-acetyl-3-nitro-5-trifluoromethyldiphenyl ether [ No CAS ]
  • 21
  • [ 99-93-4 ]
  • pinacolboratamethylenetriphenylphosphonium iodide [ No CAS ]
  • [ 4286-23-1 ]
  • 22
  • [ 99-93-4 ]
  • [ 1836-06-2 ]
YieldReaction ConditionsOperation in experiment
84.5% 40.05 g (0.24 mol) of potassium bromate and 100 ml of water were placed in a 500 ml four-necked flask,and a mixed solution of 27.24 g(0.2 mol) of p-hydroxyacetophenone and 80 g of methanol was placed in a 500 ml four-necked flask and stirred under stirring. 312 g of a 20% by weight sodium hydrogen sulfite solution was added. The dropping temperature was controlled not to exceed 70 C, the dropping time was about 3 hours, and the reaction was kept for 2 hours after the dropwise addition. It was cooled to room temperature, filtered off with suction, washed with water, and recrystallized from methanol to give 36.3 g beige solid, yield 84.5%, melting point (m.p.) = 82 ~ 85C.
39% With bromine; acetic acid; at 20℃; for 0.5h; Intermediate 15. l-(3-bromo-4-hydroxyphenyl)ethanone (15)15; [0180] To a solution of 4-hydroxyacetophenone (6.8 g, 0.05 mol, 1 eq) in 60% acetic acid (50 mL), was added a solution of bromine (2.6 mL, 0.05 mol, 1 eq) in 80% acetic acid (20 mL). After stirring at room temperature for 30 min, the reaction mixture was poured into 100 mL of cold water. The solid was filtered and the filtrate was further diluted with 500 mL of cold water. The white precipitate was collected by filtration, washed with water and dried under vacuum to afford 4.2 g (39%) of l-(3- bromo-4-hydroxyphenyl)ethanone (15) as white solid. 1HNMR (CDCl3, 400MHz): delta 8.15 (s, 1H), 7.86 (d, 1H), 7.18 (d, 1H), 5.96 (s, 1H), 2.56 (s, 3H). MS (ES-API): M+l = 216.9. HPLC (Method B) tR = 2.48 min.
39% With bromine; In acetic acid; at 20℃; for 0.5h; Intermediate 17: l-(3-bromo-4-hydroxyphenyDethanone (17)17[0162] To a solution of 4-hydroxyacetophenone (6.8 g, 0.05 mol, 1 eq) in 60% acetic acid (50 niL), was added a solution of bromine (2.6 mL, 0.05 mol, 1 eq) in 80% acetic acid (20 mL). After stirring at rt for 30 min, the reaction mixture was poured into 100 mL of cold water. The solid was filtered and the filtrate was further diluted with 500 mL of cold water. The white precipitate was collected by filtration, washed with water and dried under vacuum to afford 4.2 g (39 %) of l-(3-bromo-4- hydroxyphenyl)ethanone (17) as white solid. 1HNMR (CDCl3, 400MHz): delta 8.15 (s, IH), 7.86 (d, IH), 7.18 (d, IH), 5.96 (s, IH), 2.56 (s, 3H). MS (ES-API): M+l = 216.9. HPLC (Method B) tR = 2.48 min.
With bromine; In water; acetic acid; 1-(3-Bromo-4-hydroxy-phenyl)-ethanone A solution of 4-hydroxyacetophenone (13.6 g, 0.1 mol) in 65% acetic acid (100 mL) was treated with bromine (5.1 mL, 0.1 mol) dissolved in 80% acetic acid (50 mL) at room temperature. After addition of bromine the solution was further stirred at room temperature for 30 min and poured into 200 mL of cold water. The side product formed was filtered off and the filtrate was further diluted with 1 L of cold water. The white precipitate formed was filtered, washed several times with water and dried under vacuum. Yield: (10.4 g, 35%). 1H NMR(CDCl3) delta2.57 (s, 3H), 6.46 (s, 1H), 7.08 (d, 1H), 7.85 (d, 1H), 8.21 (s, 1H). MS 216 (M+H), C8H7O2Br

  • 23
  • [ 14779-18-1 ]
  • [ 99-93-4 ]
  • 4-{1-[(Z)-7-Methyl-benzothiazol-2-ylimino]-ethyl}-phenol [ No CAS ]
  • 24
  • [ 27000-00-6 ]
  • [ 99-93-4 ]
  • methyl (S)-2-(4-acetylphenoxy)-3-phenylpropanoate [ No CAS ]
  • 26
  • [ 3111-37-3 ]
  • [ 91-59-8 ]
  • [ 99-93-4 ]
  • 1-(3-bromo-5-ethoxy-4-hydroxyphenyl)-3-(4-hydroxyphenyl)benzo[f]quinoline [ No CAS ]
  • 27
  • 5-tert-butyl-2'-(trifluoromethoxy)biphenylyl-2-diazonium hexafluoroantimonate [ No CAS ]
  • [ 99-93-4 ]
  • [ 85013-98-5 ]
  • 28
  • [ 99-93-4 ]
  • ethynylmagnesium halide [ No CAS ]
  • [ 2657-25-2 ]
  • 30
  • [ 99-93-4 ]
  • [ 2657-25-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydroxide; benzaldehyde; In ethanol; water; 19) Preparation of 4'-hydroxychalcone STR28 2.7 g (20 mmol) of 4hydroxyacetophenone and 2.1 g (20 mmol) of benzaldehyde were added to a solution of 12 g of sodium hydroxide in 10 ml of water and 50 ml of ethanol, and the solution was refluxed for 3 h. After addition of 50 mnl of water, the solution was acidified with 90 ml of 4M hydrochloric acid and extracted with 100 ml of ether. The organic phase was dried (MgSO4) and concentrated in vacuo to give 4.82 g of a gum, from which 0.124 g of 4'-hydroxychalcone identical with that previously decribed by R, L.
  • 31
  • [ 627-42-9 ]
  • [ 99-93-4 ]
  • [ 85699-00-9 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydride; In DMF (N,N-dimethyl-formamide); at 0℃; for 2h; p-Acetylphenol (20.0 g, 147 mmol) was dissolved in DMF (200 mL). While cooling on ice, sodium hydride (6.46 g, 0.16 mol, 60% in oil) and then chloromethyl methylether (16.7 mL, 220 mmol) were added to the solution, and the mixture was stirred for 2 hours at the same temperature. The reaction solution was added with ice and saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. After the organic layer was washed with saturated brine, the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was,purified by silica gel column chromatography (n-hexane/ethyl acetate = 9/1), and 4-(methoxymethoxy)acetophenone (23.7 g, 89% yield) was obtained. FAB -MS m/z: [M+H]+ 181.1H-NMR (CDCl3) delta (ppm): 2.56 (s, 3H), 3.48 (s, 3H), 5.23 (s, 2H), 7.07 (d, J = 9.1 Hz, 2H), 7.93 (d, J = 9.1 Hz, 2H).
  • 32
  • [ 99-93-4 ]
  • [ 108-95-2 ]
  • [ 27955-94-8 ]
YieldReaction ConditionsOperation in experiment
91.3% With hydrogenchloride; zinc(II) chloride; In water; at 60℃; for 9.66667h; Synthesis method:The reactor was charged with 54.0 moles of phenol and 100 partsGrams of zinc chloride,Stirring to make it mixed evenly,Followed by slow addition over a period of 40 minutes6.5 mol of p-hydroxyacetophenone,After warming up to join Under the conditions of temperature and 60 60 min100 ml of concentrated hydrochloric acid,After the addition, the reaction was stirred for 8 h.After stirring, the temperature was lowered to 20 ° C,Dichloroethane was added,After sufficiently stirring again,filter, 55 vacuum drying 6hThe crude THPE product 1811 grams.The purity of the crude product95.0percent and yield 91.1percent. Purification method:1000 g of the crude product prepared above was added2000 ml of methanol,Heating completely dissolved,cool down,Slowly add1600 ml of water,Stirred at room temperature for 50 min to give pale yellow product;filter,drying.The dried product was dissolved in 1200 ml of methanol,After complete dissolution by heating,Add activated carbon decolorization, Filtered, the solvent evaporated,The resulting solid;The obtained solid was dissolved in 1000 ml of methanol,A solution of a mixture of sodium borohydride (5 g) and sodium sulfite (35 g) was slowly added,Light yellow powder gradually precipitation,The resulting solid was filtered,Vacuum drying 10 h at 25 ° C to give 913 g of product;The yield was 91.3percentHPLC analysis purity 99.5percent.
57.76 - 77.09% methanesulfonic acid; 3-mercaptopropionic acid; at 55℃; for 20.5h;Product distribution / selectivity; In this example, THPE was prepared from 4-hydroxyacetophenone, phenol, mercaptopropionic acid, and methane sulfonic acid. Phenol (200 grams (g)) was charged into a 500 milliliters (ml) 4-necked round bottom flask equipped with a mechanical stirrer, thermometer pocket, and a water-cooled reflux condenser with a calcium chloride guard and an air leak tube. The flask was then heated to 55 C. and maintained under nitrogen atmosphere, while stirring. Next, p-hydroxyacetophenone (34 g) and 3-mercaptopropionic acid (5.5 g) were added. The methane sulfonic acid (14.81 g) was then added in a drop wise manner over about a thirty minute period. The reaction mixture was maintained at 55 C. under nitrogen atmosphere for 20 hours. The reaction mixture was then cooled room temperature (RT, 24 C.) and the nitrogen flow was stopped. The reactants of the flask were transferred into a 1 liter (L) beaker containing ethylene dichloride (600 ml) and stirred for 2 hours. The solids were filtered to get a crude product weighing approximately 58 g. The crude product was then subjected to a purification process as described below. The purification process included stirring the crude reaction product into a methanol-water mixture (40:60 volume be volume, 120 ml) for 0.5 hours. Next the solids were filtered off, and the process was repeated with additional methanol-water (80 ml). The solids so obtained were then dissolved in methanol (120 ml). Sodium borohydride (NaBH4, 150 milligrams) was added to this mixture, followed by stirring for half an hour. The solution was then treated with 1 gram of charcoal and subsequently filtered. 280 ml of water containing sodium borohydride (0.0125percent weight by volume) was added to the filtrate over a period of 2 hours under nitrogen atmosphere. Another 120 ml of water containing 0.0125percent w/v of sodium borohydride was added to this mixture all at once and stirred for 2 hours. The solids were then filtered and washed with 100 ml of 20percent volume by volume of methanol in water. The purified solids were dried at 60 C. under vacuum to constant weight to provide 53 g of product. The ethylene dichloride used to isolate the solids was recovered by distilling the reaction mixture while maintaining the reaction temperature at 50-55 C., under vacuum, initially at 180 mm and at the end at 60 mm. The residue so obtained was recycled in the next batch; EXAMPLE 2. In this example, the residue obtained in Example 1 was recycled. Recycle 2a: The residue was used in the next batch with phenol (46.4 g), p-hydroxyacetophenone (34 g), 3-mercaptopropionic acid (2.44 g) and methane sulfonic acid (8.9 g). The reaction was carried out in a similar manner as the original batch to get a purified THPE (58.98 g). Recycle 2b: The residue obtained from the filtrate of recycle 1a was reacted in a similar manner with phenol (59 g), p-hydroxyacetophenone (34 g), 3-mercaptopropionic acid (2.44 g) and methane sulfonic acid (8.9 g) to provide a purified THPE (56.03 g). Unreacted phenol was obtained by distilling the filtrate under vacuum (distillation temperature 61-62 C. at 0.4 mm of Hg). The results of Example 1, and the recycle steps are tabulated in Table 2 below; EXAMPLE 3 In this example, THPE was prepared in accordance with Example 1 using the phenol recovered from Example 1. The results are tabulated in Table 2 below.
  • 33
  • [ 284462-54-0 ]
  • [ 349-65-5 ]
  • [ 350-46-9 ]
  • [ 99-93-4 ]
  • [ 75919-92-5 ]
YieldReaction ConditionsOperation in experiment
With CDI; 5-(Trifluoromethyl)-2-methoxyaniline was treated with CDI, followed by 4-(1-oxoisoindolin-5-yloxy)aniline according to Method C2d to afford the urea. Entry 26: 4-Hydroxyacetophenone was reacted with 4-fluoronitrobenzene according to Method A13, Step 1 to give 4-(4-acetylphenoxy)nitrobenzene.
With CDI; 5-(Trifluoromethyl)-2-methoxyaniline was treated with CDI, followed by 4-(1-oxoisoindolin-5-yloxy)aniline according to Method C2d to afford the urea. Entry 26: 4-Hydroxyacetophenone was reacted with 4-fluoronitrobenzene according to Method A13, Step 1 to give 4-(4-acetylphenoxy)nitrobenzene.
With CDI; 5-(Trifluoromethyl)-2-methoxyaniline was treated with CDI, followed by 4-(1-oxoisoindolin-5-yloxy) aniline according to Method C2d to afford the urea. Entry 26: 4-Hydroxyacetophenone was reacted with 4-fluoronitrobenzene according to Method A13, Step 1 to give 4-(4-acetylphenoxy)nitrobenzene.
  • 34
  • [ 284462-56-2 ]
  • [ 32315-10-9 ]
  • [ 5369-19-7 ]
  • [ 350-46-9 ]
  • [ 99-93-4 ]
  • [ 75919-92-5 ]
YieldReaction ConditionsOperation in experiment
Syntheses of Exemplified Compounds (see Tables for Compound Characterization) Entry 1: 4-(3-N-Methylcarbamoylphenoxy)aniline was prepared according to Method A13. According to Method C3, <strong>[5369-19-7]3-tert-butylaniline</strong> was reacted with bis(trichloromethyl)carbonate followed by 4-(3-N-Methylcarbamoylphenoxy)aniline to afford the urea. Entry 2: 4-Fluoro-1-nitrobenzene and p-hydroxyacetophenone were reacted according to Method A13, Step 1 to afford the 4-(4-acetylphenoxy)-1-nitrobenzene.
Syntheses of Exemplified Compounds (See Tables for Compound Characterization) Entry 1: 4-(3-N-Methylcarbamoylphenoxy)aniline was prepared according to Method A13. According to Method C3, <strong>[5369-19-7]3-tert-butylaniline</strong> was reacted with bis(trichloromethyl)carbonate followed by 4-(3-N-Methylcarbamoylphenoxy)aniline to afford the urea. Entry 2: 4-Fluoro-1-nitrobenzene and p-hydroxyacetophenone were reacted according to Method A13, Step 1 to afford the 4-(4-acetylphenoxy)-1-nitrobenzene.
SYNTHESES OF EXEMPLIFIED COMPOUNDS (See Tables for Compound Characterization) Entry 1: 4-(3-N-Methylcarbamoylphenoxy)aniline was prepared according to Method A13. According to Method C3, <strong>[5369-19-7]3-tert-butylaniline</strong> was reacted with bis(trichloromethyl)carbonate followed by 4-(3-N-Methylcarbamoylphenoxy)aniline to afford the urea. Entry 2: 4-Fluoro-1-nitrobenzene and p-hydroxyacetophenone were reacted according to Method A13, Step 1 to afford the 4-(4-acetylphenoxy)-1-nitrobenzene.
  • 35
  • [ 4548-45-2 ]
  • [ 284462-56-2 ]
  • [ 349-65-5 ]
  • [ 99-93-4 ]
  • 4-(4-acetylphenoxy)-5-nitropyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With CDI; According to Method C2a, 2-methoxy-5-(trifluoromethyl)aniline was reacted with CDI followed by 4-(3-N-methylcarbamoylphenoxy)aniline to afford the urea. Entry 9: 4-Hydroxyacetophenone was reacted with 2-chloro-5-nitropyridine to give 4-(4-acetylphenoxy)-5-nitropyridine according to Method A3, Step 2.
With CDI; According to Method C2a, 2-methoxy-5-(trifluoromethyl)aniline was reacted with CDI followed by 4-(3-N-methylcarbamoylphenoxy)aniline to afford the urea. Entry 9: 4-Hydroxyacetophenone was reacted with 2-chloro-5-nitropyridine to give 4-(4-acetylphenoxy)-5-nitropyridine according to Method A3, Step 2.
  • 36
  • conc. H2 SO4 [ No CAS ]
  • [ 99-93-4 ]
  • [ 6322-56-1 ]
YieldReaction ConditionsOperation in experiment
With KNO3; In n-heptane; 1. 1-[4-Hydroxy-3-nitrophenyl]ethanone To mechanically stirred conc. H2 SO4 (700 mL) at 3° C. was added p-hydroxyacetophenone (66.0 g, 480 mmol) followed by KNO3 (48.3 g, 477 mmol) in two approximately equal portions about four minutes apart. An additional 3.76 g of KNO3 was added after 1.67 hours to insure reaction completion. The reaction was slowly poured into 8 L crushed ice/water and extracted with 4 L ethyl acetate (EtOAc). The extract was concentrated in vacuo to a volume of ~1.25 L, 500 mL heptane were added and concentration was continued. Once a thick yellow suspension formed at 50° C., it was cooled to ~10° C. and filtered. The collected solids were washed with ~150 mL heptane and dried in vacuo at ~40° C. to give 81.8 g of the title compound.
  • 37
  • [ 102908-37-2 ]
  • [ 99-93-4 ]
  • [ 1078710-31-2 ]
  • 38
  • [ 97-94-9 ]
  • [ 1836-06-2 ]
  • [ 22934-47-0 ]
  • [ 99-93-4 ]
  • 39
  • [ 7789-45-9 ]
  • [ 99-93-4 ]
  • [ 61791-99-9 ]
YieldReaction ConditionsOperation in experiment
First, 4 -hydroxyacetophenone is allowed to react with cupric bromide in accordance with ordinary methods, for example, the method described in a literature,, to prepare 2-bromo-4 -hydroxyacetophenone (
  • 41
  • [ 50-00-0 ]
  • [ 99-93-4 ]
  • [ 51639-48-6 ]
  • [ 1292319-35-7 ]
YieldReaction ConditionsOperation in experiment
69.6% In ethanol; at 120℃; General procedure: To a solution of hydroxy-substituted acetophenone and paraformaldehyde in EtOH (75 mL) was added 4-piperazinoacetophenone at rt as per reported earlier literature.[16], [17], [18] and [19] Then the resulting mixture was heated to reflux for 18-22 h at 120 C. On completion, the reaction mixture was concentrated under reduced pressure and the crude product was purified by column chromatography to yield the ortho substituted Mannich base in good yield (Scheme 1).
  • 42
  • [ 1435-48-9 ]
  • [ 99-93-4 ]
  • [ 129644-21-9 ]
  • 43
  • [ 50-00-0 ]
  • [ 15572-56-2 ]
  • [ 99-93-4 ]
  • [ 1309372-61-9 ]
  • 44
  • [ 149104-90-5 ]
  • [ 6322-56-1 ]
  • [ 98-86-2 ]
  • [ 100-19-6 ]
  • [ 99-93-4 ]
  • 45
  • [ 22080-96-2 ]
  • [ 99-93-4 ]
  • [ 1413765-55-5 ]
  • 46
  • [ 22080-96-2 ]
  • [ 99-93-4 ]
  • 3-(4-hydroxy-2,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)propan-1-one [ No CAS ]
  • 47
  • [ 61296-22-8 ]
  • [ 99-93-4 ]
  • [ 1384191-76-7 ]
YieldReaction ConditionsOperation in experiment
24.4% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 24h; l-[4-(2-Amino-thiazol-5-yloxy)-phenyl]-ethanone l -|4-(2-Amino-thiazol-5-yloxy)-phenyl]-ethanone A m ixture of 2-Am ino-5-bromothiazole monohydrobrom ide ( 1 0 g, 0.0384 mol), 4- hydroxyacetophenone (5.24 g, 0.0384 mol), potassium carbonate ( 1 3.3 g. 0.0962 mol) in 1 00 m l of N.lM-dimethylformamide was stirred at room temperature for 24 hours. The reaction mixture was diluted with water, extracted with ethyl acetate. The combined organic layer was washed with water, brine, dried over anhydrous sodium sulphate and evaporated. The crude material was purified by column chromatography (silica gel 100- 200 mesh, 40:60 ethylacetate:hexane) to afford 1-[4-(2-Amino-thiazol-5-yloxy)-phenyl|- 5 ethanone in 24.4 % yield. LCMS-[ +H] 235.4, ? NMR (400 MHz, CDC13): 7.960-7.982. (d, 2H, J=8.8 Hz), 7.149- 7.170 (d, 211, 8.4 Hz), 6.897 (s, 2H), 6.772 (s, lH), 2.485 (s, 1H).
  • 48
  • [ 99-93-4 ]
  • [ 867367-02-0 ]
  • 49
  • [ 1668-54-8 ]
  • [ 99-93-4 ]
  • [ 1465740-18-4 ]
  • 50
  • [ 165253-29-2 ]
  • [ 99-93-4 ]
  • [ 1250570-27-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In ethanol; at 20℃; for 48h; General procedure: A mixture of 1-(4-hydroxyphenyl)ethanone (1.0 g), potassium carbonate ( 2.1 g ), 1-bromo-2-methylpropane (1.1 g) was stirred in ethanol at room temperature for 2 days. The reaction mixture was filtered, the filtrate was concentrated. The residue was purified by column chromatography with petroleum ether: ethyl acetate (15:1) as eluent to afford the desired product (165mg, yield 11.7percent).
  • 51
  • [ 50-00-0 ]
  • [ 6091-44-7 ]
  • [ 99-93-4 ]
  • [ 4006-70-6 ]
YieldReaction ConditionsOperation in experiment
45% In acetic acid; at 120℃; for 0.333333h;Microwave irradiation; General procedure: A ketone compound, paraformaldehyde and suitable amine were taken in 1:1.2:1 mol ratios and heated in 10 mL of glacial acetic acid at 120 C at 70 Watt for series A and B for several times. The reactions were monitored by TLC using CHCl3: MeOH (9:1 or 8:2) as a solvent system. The compounds were purified by crystallisation. Chemical structures of the compounds were confirmed by 1H NMR (data were not present) and their reported melting points. Amine part was morpholine in Series A (1-9) and <strong>[6091-44-7]piperidine</strong> in Series B (10-18). Physical data of the compounds obtained by microwave irradiation method are reported in Table 2 (See Supplementary File).
  • 52
  • [ 5467-74-3 ]
  • [ 99-93-4 ]
  • [ 5731-01-1 ]
  • 53
  • [ 34800-90-3 ]
  • [ 99-93-4 ]
  • C20H18N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.5% In ethanol;Reflux; General procedure: solutionof acid hydrazide (0.01 mol) and appropriate benzaldehyde/acetophenone (0.01 mol) in ethanol was refluxed for 5-6 h. The precipitated title compounds were then filtered off, washed with water and recrystallized from ethanol.
  • 54
  • [ 4687-25-6 ]
  • [ 99-93-4 ]
  • trans-3-(benzofuranyl)-1-(4-hydroxyphenyl)-2-propen-1-one [ No CAS ]
  • 55
  • [ 92-55-7 ]
  • [ 99-93-4 ]
  • C13H9NO5 [ No CAS ]
  • 56
  • [ 92-55-7 ]
  • [ 99-93-4 ]
  • (3'R,4'R)-4'-(4-hydroxybenzoyl)-1'-methyl-3'-(5-nitro-2-furyl)spiro[indene-2,2'-pyrrolidine]-1,3-dione [ No CAS ]
  • 57
  • [ 13674-16-3 ]
  • [ 99-93-4 ]
  • 2-[4-(1-hydroxyiminoethyl)phenoxy]-3-phenylpropanoic acid [ No CAS ]
  • 58
  • [ 13674-16-3 ]
  • [ 99-93-4 ]
  • methyl 2-(4-acetylphenoxy)-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;Cooling with ice; Inert atmosphere; General procedure: A solution of diisopropylazodicarboxylate (DIAD, 10 mmol) in anhydrous THF (20 mL) was added dropwise to an ice-bath cooled mixture of ethyl or methyl phenyllactate (10 mmol), the suitable phenol (10 mmol) and PPh3 (10 mmol) in anhydrous THF (50 mL). The reaction mixture was stirred overnight, under N2 atmosphere, at room temperature. The organic solvent was evaporated in vacuo, and a mixture of Et2O and n-hexane (40 mL, 1:1) was added to the residue. The resulting precipitate was filtered off, and the filtrate was evaporated to dryness. The residue was chromatographed on a silica gel column using the suitable eluent affording the desired compounds in 33-79% yields.
  • 60
  • [ 1120-95-2 ]
  • [ 99-93-4 ]
  • 1-(4-(pyridazin-3-yloxy)phenyl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 1h;Microwave irradiation; A mixture of 1-(4-hydroxyphenyl)ethanone (283 mg, 2.08 mmol), <strong>[1120-95-2]3-<strong>[1120-95-2]chloropyridazine</strong></strong> (238 mg, 2.08 mmol) and potassium carbonate (574 mg, 4.16 mmol) in DMF (5 mL) is irradiated in a microwave reactor (Biotage Initiator) for 60 mm. at 140 oC. After cooling, the reaction mixture is filtered through Celite pad and the filter cake is washed with EtOAc. The filtrate and washings are washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by column chromatography (Biotage) on silica gel (25 g) eluting with 10-80percent ethyl acetate in DCM to give the the titled compound (58 mg, 13percent yield) as a white solid.1HNMR (270 MHz, DMSO-d6): delta 9.07 (dd, J = 4.6, 1.3 Hz, 1H), 8.06 (d, J = 8.5 Hz, 2H), 7.84 (dd, J = 9.2, 4.6 Hz, 1H), 7.59-7.55 (m, 1H), 7.36 (d, J = 8.5 Hz, 2H), 2.60 (s, 3H).MS (ESI) mlz: 215.1 (M+H)÷.
13% With potassium carbonate; In d7-N,N-dimethylformamide; at 140℃; for 1h;Microwave irradiation; A mixture of i-(4-hydroxyphenyl)ethanone (283 mg, 2.08 mmol), <strong>[1120-95-2]3-<strong>[1120-95-2]chloropyridazine</strong></strong> (238 mg, 2.08 mmol) and potassium carbonate (574 mg, 4.16 mmol) in DMF (5 mL) was iffadiated in a microwave reactor (Biotage Initiator) for 60 mm. at 140°C. After cooling, the reaction mixture was filtered through Celite pad and the filtrate was washed with EtOAc. The filtrate was diluted with water and the organic layer was separated. After the extraction of the aqueous layer with EtOAc, the combined organic layers were washed with brine, dried over sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (Biotage) on silica gel (25 g) eluting with 10-80percent EtOAc in DCM to give the titled compound (58 mg, 13percent yield) as a white solid.1HNMR (270 MHz, DMSO-d6): delta 9.07 (dd, J = 4.6, 1.3 Hz, 1H), 8.06 (d, J = 8.5 Hz, 2H), 7.84 (dd, J = 9.2, 4.6 Hz, 1H), 7.59-7.55 (m, 1H), 7.36 (d, J = 8.5 Hz, 2H), 2.60 (s, 3H).
  • 61
  • [ 446-51-5 ]
  • [ 99-93-4 ]
  • [ 93291-62-4 ]
  • 62
  • [ 346-06-5 ]
  • [ 99-93-4 ]
  • 1-(4-((2-(trifluoromethyl)benzyl)oxy)phenyl)ethanone [ No CAS ]
  • 63
  • [ 349-75-7 ]
  • [ 99-93-4 ]
  • [ 79615-77-3 ]
  • 64
  • [ 100-52-7 ]
  • [ 99-93-4 ]
  • [ 2657-25-2 ]
  • [ 102692-58-0 ]
  • 65
  • [ 1480-65-5 ]
  • [ 99-93-4 ]
  • C13H10ClNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 6h; General procedure for the synthesis of ClA mixture of 4?-hydroxyacetophenone (5.00 g, 36.7 mmol), <strong>[1480-65-5]5-chloro-2-fluoropyridine</strong> (5.79 g, 44.0 mmol) and K2C03 (10.1 g, 73.4 mmol) in DMF (150 mL) was stirred at 100 °C for 6 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc (200 mL), then filtered and the filtrate was washed with brine (150 mL x3), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford a residue. The residue was washed with PE/ EtOAc = 20/1(40 mL) to afford Cl.
  • 66
  • [ 173471-71-1 ]
  • [ 99-93-4 ]
  • (E)-3-(6-(dimethylamino)naphthalen-2-yl)-1-(4-hydroxyphenyl)prop-2-en-1-one [ No CAS ]
  • 67
  • [ 67-56-1 ]
  • [ 99-93-4 ]
  • [ 32136-81-5 ]
  • 68
  • [ 22927-13-5 ]
  • [ 99-93-4 ]
  • 3-(2-ethylphenyl)-1-(4-hydroxyphenyl)propenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% General procedure: To the solution of (0.05 mol, 6.8 g) of 1-(4-Hydroxy-phenyl)-ethanone (1) in 30 ml of methanol on an ice bath, freshly prepared2 N methanolic NaOH solution (50 ml) was added and stirred for20 min. To this 0.05 mol of appropriate aldehyde (2a-l) was addedand the reaction mixture was stirred at room temperature for20-24 h. The reaction mixture was cooled in an ice bath andneutralized with dilute hydrochloric acid. The obtained precipitatewas separated by filtration and washed with distilled water to givethe crude product. The product (3a-o) so obtained was recrystallizedfrom 75% methanol. The purity of the products was checkedon TLC by using a mixture of ethyl acetate and hexane as mobilephase.4.2.1. 3-(2-Ethyl-phenyl)-1-(4-hydroxy-phenyl)-propenone (3a)Prepared by the above method from 2a (0.05 mol, 6.6 ml) and 1(0.05 mol, 6.8 g); yield: 72% as pale yellow crystalline solid;Rf = 0.64 in EtOAc/hexane, 3:7; mp: 202-204 C. FTIR (neat) mmax:3085 (CH, aromatic), 767 (CH, substituted phenyl ring), 1686(CO), 1640 (CC, conjugated to CO), 1590 ( , aromatic),2961-2835 (CH), 1443 (CH); 1H NMR (300 MHz, d): 5.1(s, 1H,ArAOH), 6.9 (m, 2H, ArH), 7.55 (m, 2H, ArH), 7.44 (d, 1H, 1-ethylene,J = 7.3 Hz), 8.25 (d, 1H, 1-ethylene, J = 6.4 Hz), 7.1 (m, 3H,ArH), 7.25 (d, 1H, ArH, J = 6.9 Hz), 2.55 (m, 2H, methylene), 1.25(t, 3H, methyl, J = 7.4 Hz).
  • 69
  • [ 22927-13-5 ]
  • [ 99-93-4 ]
  • [5-(2-ethylphenyl)-3-(4-hydroxyphenyl)-4,5-dihydropyrazol-1-yl]pyridin-3-yl-methanone [ No CAS ]
  • 70
  • [ 28785-06-0 ]
  • [ 99-93-4 ]
  • 1-(4-hydroxyphenyl)-3-(4-propylphenyl)propenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% General procedure: To the solution of (0.05 mol, 6.8 g) of 1-(4-Hydroxy-phenyl)-ethanone (1) in 30 ml of methanol on an ice bath, freshly prepared2 N methanolic NaOH solution (50 ml) was added and stirred for20 min. To this 0.05 mol of appropriate aldehyde (2a?l) was addedand the reaction mixture was stirred at room temperature for20?24 h. The reaction mixture was cooled in an ice bath andneutralized with dilute hydrochloric acid. The obtained precipitatewas separated by filtration and washed with distilled water to givethe crude product. The product (3a?o) so obtained was recrystallizedfrom 75percent methanol. The purity of the products was checkedon TLC by using a mixture of ethyl acetate and hexane as mobilephase.
  • 71
  • [ 28785-06-0 ]
  • [ 99-93-4 ]
  • [3-(4-hydroxyphenyl)-5-(4-propylphenyl)-4,5-dihydropyrazol-1-yl]pyridin-3-yl-methanone [ No CAS ]
  • 72
  • [ 354-08-5 ]
  • [ 99-93-4 ]
  • [ 83882-67-1 ]
  • 73
  • [ 5629-98-1 ]
  • [ 99-93-4 ]
  • C15H10Br2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In ethanol; water; for 4h; General procedure: A suspension of aromatic aldehyde 1 (40 mmol) and aromaticketone 2 (40 mmol) in mixture of 10 ml saturatedNaOH solution in water and 10 ml ethanol was stirred for 4 hat 20 C to obtain pure chalcone 3 (Ozdemir et al. 2007;Chimenti et al. 2010). Further, mixture of chalcone 3 (10mmol) and thiosemicarbazide (20 mmol) was refluxed understirring with KOH (20 mmol) in 70mL EtOH for approximately6 h to get N-thiocarbamoyl pyrazole derivative 4(Scheme 1). This N-thiocarbamoyl pyrazole derivative 4 (10mmol) was added in appropriate quantity of EtOAc and wasrefluxed with ethyl bromoacetate (30 mmol) for 1.5 h (EISabbaghet al. 2009; Seebacher et al. 2003). After completionof reaction, the reaction mixture was mixed with CHCl3and allowed to evaporate to obtain pyrazol-1-yl-1,3-thaizol-4(5H)-one derivative (5a-5m, Fig. 2). The refined compoundwas obtained by subsequent purification withrecrystallization by using ethanol-acetone (1:1).
  • 74
  • [ 82294-70-0 ]
  • [ 99-93-4 ]
  • C13H11NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium hydroxide; In ethanol; at 20℃; for 18h; Hydroxychalcone was prepared by Claisen-Schmidt condensation of <strong>[82294-70-0]4-methylthiazole-5-carbaldehyde</strong> (1.0 g, 7.87 mmol) and 4-hydroxyacetophenone (1.07 g, 7.87 mmol) in the presence of sodium hydroxide in ethanol, as reported in the literature. Yield: 90%; mp: 102-105 C; 1H NMR (300 MHz, DMSO-d6): deltaH 2.51 (s, 3H); 6.90 (d, J 8.4 Hz,2H); 7.47 (d, J 15.0 Hz, 1H); 7.85 (d, J 15.0 Hz, 1H); 8.02 (d, J 8.4 Hz, 2H); 9.11(s, 1H); 10.50 (bs, 1H). 13C NMR (75 MHz, DMSO-d6): deltac 15.4, 115.4, 123.4, 128.7, 131.1, 131.9, 154.7, 156.2, 162.3, 186.2.
  • 75
  • [ 80-05-7 ]
  • [ 4286-23-1 ]
  • [ 123-08-0 ]
  • [ 99-93-4 ]
  • 3-(4-Hydroxyphenyl)-3-methyl-2-oxobutanoic acid [ No CAS ]
  • 76
  • [ 10320-42-0 ]
  • [ 99-93-4 ]
  • 1-(4-((5-nitropyrimidin-2-yl)oxy)phenyl)ethane-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% a vacuum 50ml reaction bottle is vacuumed three times, then added to the reaction bottle1-(4-Hydroxyphenyl)ethane-1-one (150 mg, 1.0 mmol, 1.0 equiv), was added with 3.0 ml of dry THF.All the 1-(4-hydroxyphenyl)ethane-1-one was dissolved, and then NaH (28.8 mg, 1.2 mmol, was added to the reaction flask under ice bath.1.2equiv, 60percent sodium hydride content suspended in mineral oil), reacted in an ice bath for 30 min; then into the reaction jar<strong>[10320-42-0]<strong>[10320-42-0]2-Chloro-5-nitropyrimidin</strong>e</strong> (0.1593 g, 1.0 mmol, 1.0 equiv) was added. Slowly raise the temperature of all the mixture to 50 °CDegree reaction for 12 hours. The reaction was monitored by TLC, and the reaction was stopped if it was detected that all of the phenol was completely reacted.The experimental treatment was to drain the solution in the reaction; dissolve the solute in the reaction flask with ethyl acetate and transfer to 100 ml.In a round bottom flask, add 3 ml (200-300 mesh) of silica gel to a round bottom flask for spin-drying (petroleum ether and ethyl acetate) over silica gel.In the column. Wait until the intermediate product white crystal 1-(4-((5-nitropyrimidin-2-yl)oxy)phenyl)ethane-1-one (207mg90percent yield).
  • 77
  • [ 5736-88-9 ]
  • [ 99-93-4 ]
  • (E)-3-(4-butoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With water; sodium hydroxide; In ethanol; at 5 - 25℃;Inert atmosphere; General procedure: An aqueous solution of NaOH (20%, 5mL) was added dropwise to a previously cooled mixture of selected acetophenone (5mmol) and selected (hetero)aryl aldehydes (5mmol) in EtOH (25mL) under vigorous stirring. The mixture was stirred at RT for 24-72h. After completion of the reaction (as indicated by TLC), the mixture was poured onto crushed ice and acidified with dilute HCl. The precipitated product was filtered at suction and washed to neutral filtrate. The solid was recrystallized from EtOH to get crystalline product.
64% With sodium hydroxide; In ethanol; at 20℃;Inert atmosphere; General procedure: A solution of NaOH (20%) (5mL) was added dropwise to a previously cooled mixture of 10mmol of substituted acetophenone and 10mmol of substituted carbaldehyde in 25mL ethanol under vigorous stirring. The mixture was stirred at room temperature for 24-72h. After completion of the reaction as indicated by TLC, the mixture was poured onto crushed ice and acidified with dil. HCl. The precipitate obtained was filtered by suction and washed to neutral. The solid was recrystallized from ethanol/acetone to get crystalline chalcone.
  • 78
  • [ 5736-88-9 ]
  • [ 99-93-4 ]
  • (E)-2-(4-(3-(4-butoxyphenyl)acryloyl)phenoxy)-N-(1-oxo-1,3-dihydroisobenzofuran-5-yl)acetamide [ No CAS ]
  • 79
  • [ 99-93-4 ]
  • [ 4286-23-1 ]
  • 80
  • [ 41014-43-1 ]
  • [ 99-93-4 ]
  • 1-(4-(benzo[d]oxazol-2-ylmethoxy)phenyl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
49.44% With potassium carbonate; In acetone; for 4h;Reflux; General procedure: To a solution of various substituted phenols (1 mmol) in dry acetone (30 mL) K2CO3 (1 mmol)and compound 3 or 4 (1 mmol) were added. After being stirred for 4 h at reflux temperature, thereaction mixture was cooled, filtered, and concentrated under vacuum. Then the residue was dilutedwith 30 mL ethyl acetate and sequentially washed with 30 mL 1 M HCl, aq. NaHCO3 solution andbrine in order. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification of theresidue by chromatography on silica gel furnished target compounds. 1H-NMR, 13C-NMR and massspectroscopy (MS) of compounds 5a-m and 6a-m are shown in Supplementary Materials.
  • 81
  • [ 39250-90-3 ]
  • [ 99-93-4 ]
  • C18H18O3 [ No CAS ]
  • 82
  • [ 4903-09-7 ]
  • [ 99-93-4 ]
  • C16H13ClO3 [ No CAS ]
  • 83
  • [ 82294-70-0 ]
  • [ 99-93-4 ]
  • C13H11NO2S [ No CAS ]
  • 84
  • [ 3638-04-8 ]
  • [ 99-93-4 ]
  • 2-(4-acetylphenoxy)-4-chloro-6-methoxy-1,3,5-triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; General procedure: Phenol (ca. 500 mg, 1.0 eq) in dichloromethane(5 mL) and N,N-diisopropylethylamine (1.0 eq) in dichloromethane(5 mL) were added dropwise to a solution of 2 (1.0 eq)in dichloromethane (10 mL). The mixture was stirred for30 min at room temperature, washed with aqueous hydrochloricacid and brine, dried over sodium sulfate and concentrated.The residue was purified by silica gel column chromatographyor recrystallization.
  • 85
  • [ 1493-11-4 ]
  • [ 99-93-4 ]
  • [ 85013-98-5 ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere; General procedure: To a solution of hydroxyacetophenone (1 eq) in dry THF were addedalcohol (1 eq) and triphenylphosphine (PPh3) (1.2 eq). The reactionmixture was allowed to stir at 0 C (ice bath) for 15 min. Diisopropylazodicarboxylate (DIAD) (1.2 eq) was added dropwise into the coldsolution, and then stirred at room temperature overnight under N2. Themixture was diluted with water and extracted with ethyl acetate twice,and the combined organic phase was washed with brine solution, driedwith Na2SO4, filtrated, and concentrated under reduced pressure. Theresidue was purified on a silica gel column.
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