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CAS No. : | 589-18-4 | MDL No. : | MFCD00004664 |
Formula : | C8H10O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KMTDMTZBNYGUNX-UHFFFAOYSA-N |
M.W : | 122.16 | Pubchem ID : | 11505 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 37.54 |
TPSA : | 20.23 Ų |
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) : | -5.92 cm/s |
Log Po/w (iLOGP) : | 1.65 |
Log Po/w (XLOGP3) : | 1.58 |
Log Po/w (WLOGP) : | 1.34 |
Log Po/w (MLOGP) : | 1.87 |
Log Po/w (SILICOS-IT) : | 2.16 |
Consensus Log Po/w : | 1.72 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.02 |
Solubility : | 1.17 mg/ml ; 0.00955 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.62 |
Solubility : | 2.96 mg/ml ; 0.0242 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.57 |
Solubility : | 0.331 mg/ml ; 0.00271 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With tert.-butylhydroperoxide; copper(II) acetate monohydrate; calcium carbonate In acetonitrile at 80℃; for 24 h; | General procedure: An oven-dried 15 mL glass vial with a magnetic stirrer bar was charged with Cu(OAc)2·H2O (12 mg, 6 molpercent), N,O-dimethylhydroxylamine hydrochloride (2; 117 mg, 1.2 mmol), the respective benzyl alcohol 1 (1 mmol), aq 70percent TBHP (0.17 mL, 1.2 mmol), CaCO3 (120 mg, 1.2 mmol) in MeCN (1 mL). The glass vial was flushed with N2 three times and the contents were stirred at r.t. for 1 h. Then the reaction mixture was stirred for 24 h at 80 °C. After completion of the reaction, the mixture was cooled to r.t. All volatiles were removed under vacuum. The product was extracted with EtOAc (20 mL) and the organic layer was washed with sat. aq NaHCO3 (20 mL), dried (Na2SO4), and the solvent removed under vacuum. The Weinreb amide product 3 was purified by column chromatography (silica gel, 100–200 mesh) using a gradient of petroleum ether (bp 60–80 °C) and EtOAc. All the amides were identified by GC-MS, 1H, and 13C NMR spectroscopic analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With H3[P(Mo3O10)4]*nH2O at 20℃; for 0.05h; | |
98% | With SBA-15-Ph-Pr-SO3H at 20℃; for 0.166667h; | |
98% | With 1,3,5-tribromo-1,3,5-triazinane-2,4,6-trione In neat (no solvent) at 20℃; for 0.416667h; | Acetylation of benzyl alcohol using aceticanhydride catalyzed by tribromoisocyanuric acid General procedure: To a mixture of the benzyl alcohol (1 mmol)and acetic anhydride (3 mmol); 0.074 gtribromoisocyanuric acid (0.2 mmol) was added. Thereaction mixture was stirred at room temperaturefor 12 min. After completion of the reaction (TLC),dichloromethane (10 mL) was added to the reactionmixture and filtered. The product was extracted withH2O (3×10 mL), and the organic layer was driedover anhydrous Na2SO4salt. Then solvent wasevaporated to dryness to afford the pure product. |
96% | With [SnIV(TNH2PP)(OTf)2]*CMP In acetonitrile at 20℃; for 0.1h; | |
95% | With thalium(III) chloride tetrahydrate at 20℃; for 0.133333h; | |
95% | With cadmium(II) oxide at 80℃; for 0.166667h; Neat (no solvent); Microwave irradiation; | |
93% | With colloidal gold nanoparticle-supported gadolinium complex In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation; | MW-Assisted RS-Au-L-Gd (3)-Catalyzed Acetylation of Alcohols General procedure: A mixture of colloidal AuNP-surface-bound Gd catalyst RS-Au-L-Gd (3)(2.0×10-3mmol Gd), alcohol (0.5 mmol), and acetic anhydride (5 mmol) in DMF (80 µL) was placed in the reaction vessel under 300 W MW (CEM single-mode Discover Labmate System) for 60 s. After the reaction, the resulting mixture was used directly for 1H NMR analysis for the analytic yield. |
93% | With polystyrene-nanoencapsulated FeCl3 catalyst In acetonitrile at 20℃; for 0.5h; | 2.3. A typical experimental procedure for the acetylation of alcohols, phenols, amines, and thiols with Ac 2 O catalyzed by PS-NC/ FeCl 3 General procedure: In a single-round bottomed flask (25 mL) containing a mixture of alcohol or phenol (1 mmol) and acetic anhydride (2 mmol) in CH 3 CN (4 mL) was added PS-NC/FeCl 3 (60 mg, 3.55 mol%, with respect to iron(III) content and the resulting heterogeneous mix- ture was stirred at room temperature for the time indicated in the Table ( 2 ). Upon completion of the reaction as monitored by TLC, the reaction mixture was filtered and the nanocapsules rinsed with CH 3 CN and methanol. The filtrate was washed with distilled water after quenching with a saturated solution of NaHCO 3 , dried over anhydrous MgSO 4 , and concentrated under reduced pressure us- ing a rotary evaporator to obtain the almost pure acetate products. It should be pointed out that the filtrate was analyzed at each run by ICP and atomic absorption spectroscopy to determine the leach- ing of the Fe(III) component. All products were characterized by a comparison of their spectral data (IR and 1 HNMR) and compared with the literature data. Nanoencapsulated catalyst recovery / reuse experiment, and determination of Fe in PS-NC / FeCl 3 by ICP analysis are given in ESI. |
91% | With 4-imidazol-1-ylbutane-1-sulfonic acid at 50℃; for 0.0833333h; | Typical procedure for acetylation of alcohols, phenols,amines, and thiols General procedure: In a 25-mL round bottom flask, a mixture of the substrate(2.0 mmol), acetic anhydride (4.0 mmol), and ImBuSO3H (2mL) was stirred at 50 C for an appropriate time. After completionof the reaction (monitored by TLC), the mixture wasextracted with Et2O (5 5 mL) and the supernatant etherealsolution was decanted off. The dual solvent-catalystImBuSO3H was allowed to remain in the flask and freshreagents could be added and the reaction could be run again.The combined ethereal solution were concentrated in vacuoto give the acetylated product identical (IR, 1H and 13CNMR and GC-MS) to an authentic sample. |
90% | at 50℃; for 1h; | |
88% | With C17H14F17N2(1+)*I(1-) In neat (no solvent) at 20℃; for 24h; Sealed tube; | Typical procedure for fluorous DMAP 3b catalyzed acylation General procedure: A sealed tube was charged with fluorous DMAP 3b (69.6 mg, 0.1 mmol), benzyl alcohol (108 mg, 1 mmol), and Ac2O (113 mg, 1.1 mmol). The reaction mixture was stirred at room temperature for 24 h. Hexane (4 mL) was added, and the stirring was maintained for 10 min. After decantation, the hexane phase was removed, and the remaining catalyst (yellowish paste) can be reused for a further catalysis. The acylation product contained in the hexane phase was purified by distillation to afford 136 mg of benzyl acetate (91% yield). |
83% | With 1H-imidazole for 0.05h; Irradiation; microwave; | |
48% | at 85℃; for 15h; Inert atmosphere; | |
With pyridine at 20℃; | ||
With sodium acetate | ||
With phosphoric acid at 20℃; | ||
100 %Chromat. | With [tetrabutylammonium]8 5,10,15,20-tetrakis(4-hexamolybdato)-porphyrinatotin(IV) chloride In acetonitrile at 20℃; for 0.0666667h; | |
66 %Chromat. | With Magnetically separable γ-Fe2O3 nanoparticles In neat (no solvent) at 28℃; for 1h; Sealed tube; Sonication; | 2.4. General procedure for acylation reaction General procedure: A 25mL sealed tube containing a magnetic stir bar was charged with phenol/alcohol/amine (1mmol) and acetic anhydride (1.5mmol), nano γ-Fe2O3 (5mol%, 8mg) as catalyst. The reaction mixture was kept for sonication in sonication bath at room temperature (28°C) for 1h. The ultrasonic bath (Labman Scientific Instruments, Model - LMUC 4) had a frequency of 33kHz and electric power rating of 100W. The reaction progress was monitored on thin-layer chromatography (TLC) and gas chromatography (PerkinElmer, GC Clarus 400) analysis. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and catalyst was separated from reaction mixture by using a strong magnet. The separated catalyst was washed with distilled water and absolute ethanol several times then dried in oven and reused for further reaction. The reaction mixture was washed with saturated NaHCO3 solution (1×15mL) and the product was extracted with ethyl acetate (3×10mL) and dried over Na2SO4 and evaporated under vacuum. All the obtained products are well known in the literature and were confirmed by gas chromatography-mass spectrometry (Shimadzu GCMS-QP 2010) analysis by comparison with literature data. |
95 %Chromat. | With zirconium(IV) chloride nanoencapsulated in polystyrene In acetonitrile at 20℃; for 0.416667h; | 2.3 Typical Experimental Procedure fortheAcylation ofAlcohols andPhenols withAc2O Catalyzed byPS-NC ZrCl4 General procedure: In a single-round bottomed fask (25mL) containing a mixture of alcohol or phenol (1mmol) and acetic anhydride (1.5mmol) in CH3CN (4mL) was added PS-NC ZrCl4 (80mg, ~ 4mol%, with respect to zirconium(IV) content) and the resulting heterogeneous mixture was stirred at room temperature for the time indicated in the Table2. Upon completion of the reaction as monitored by TLC, the reaction mixture was fltered and the nanocapsules rinsed with CH3CN and methanol. The fltrate was washed with distilled water after quenching with a saturated solution of NaHCO3, dried over anhydrous MgSO4, and concentrated under reduced pressure using a rotary evaporator to obtain the almost pure acetate products. It should be pointed out that the fltrate was analyzed at each run by ICP and atomic absorption spectroscopy to determine the leaching of the zirconium(IV) component. All products were characterized by a comparison of their spectral data (IR and 1 HNMR) and compared with the literature data. The details of the determination of Zr in PS-NC/ZrCl4 nanocapsules by ICP analysis are given in ESI. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dmap; In dichloromethane; acetonitrile; at 0 - 20℃; for 3h; | To a stirred solution of p-tolylmethanol (70.0 g, 570 mmol) in DCM/MeCN (1 : 1, v/v, 1400 mL) was added bis(2,5-dioxopyrrolidin-l-yl) carbonate (146.8 g, 570 mmol) and DMAP (35.0 g, 285 mmol) at 0-5 C. The mixture was allowed to warm up to room temperature. After stirring at room temperature for 3 hours, the mixture was concentrated under reduced pressure. The residue was dissolved in DCM (1500 mL), washed with water, brine, dried over sodium sulfate, and the organic phase was concentrated under reduced pressure. The concentrate was triturated with hexane/ethyl acetate (2: 1, v/v) to afford the title compound as a white solid (120 g, 80%). 1H MR (400 MHz, CDC13) delta 7.29 (d, J= 8.0 Hz, 2H), 7.20 (d, J= 8.0 Hz, 2H), 5.27 (s, 2H), 2.81 (s, 4H), 2.36 (s, 3H). |
66% | With dmap; In dichloromethane; acetonitrile; at 20℃; for 2h; | A mixture of p-tolylmethanol (2.40 g, 19.6 mmol) and bis(2,5-dioxopyrrolidin-1-yl) carbonate (5.03 g, 19.6 mmol) in a mixed solvent comprised of acetonitrile (30 mL) and CH2CI2 (30 mL) was treated with 4-dimethylaminopyridine (1.20 g, 9.8 mmol). The reaction mixture was stirred for 2 h at room temperature. After the alcohol was consumed, the mixture was poured into water (100 mL), and the organic layer was separated, dried over anhydrous sodium sulfate and concentrated under vacuum. The solid thus obtained was triturated with ether and dried to afford the title compound as a white solid (3.40 g, 66%). 1H NMR (400 MHz, CDCI3) 7.29 (d, J = 8.0 Hz, 2H), 7.20 (d, J = 8.0 Hz, 2H), 5.28 (s, 2H), 2.82 (s, 4H), 2.36 (s, 3H). |
With triethylamine; In dichloromethane; water; | Example 51 Preparation of N'-Methyl-3-(4-methylbenzyloxycarbonylamino)benzamide (Compound No. 51 in Table 2) 4-Methylbenzylalcohol (307 mg) and di(N-succinimidyl)carbonate (966mg) were dissolved in methylene chloride (20 ml), and triethylamine (0.70 ml) was added to the solution. After stirring for 4 hours at room temperature, water was added and an aqueous layer was extracted with methylne chloride. The extracted aqueous layer was successively washed with an aqueous saturated sodium chloride solution, an aqueous saturated sodium bicarbonate solution, an aqueous saturated sodium chloride solution, 2N hydrcroric acid, and an aqueous saturated sodium chloride solution, and dried over magnesia sulfite. After removing magnesium sulfate by titration, the filtrate was concentrated to obtain N-(4-methylbenzyloxycarbonyloxy)succinate imide (664 mg) as an intermediate. |
With hydrogenchloride; triethylamine; In dichloromethane; water; | Example 1 Preparation of N'-methyl-3-(4-methylbenzyloxy carbonylamino)benzamide (Compound No.51 in Table 1) After dissolving 307 mg of 4-methylbenzylalcohol and 966 mg of di(N-succinimidyl) carbonate in 20 ml of methylene chloride, adding 0.70 ml of triethylamine and stirring for 4 hours at room temperature, water was added. The aqueous layer was extracted with methylene chloride, and the extract was successively washed with saturated saline, saturated sodium bicarbonate, saturated saline, 2N hydrochloric acid and saturated saline and then dried with magnesium sulfate. After removing the magnesium sulfate by filtration, the filtrate was concentrated to obtain 664 mg of N-(4-methylbenzyloxycarbonyloxy)succinate imide as an intermediate. | |
HCl gas was bubbled through a solution of cis-8 (560 mg, 1.81 mmol) in EtOAc (3 mL) for about 45 min. The mixture was then concentrated under reduced pressure and the crude amine hydrochloride was dissolved in dry DMF (5 mL). DIPEA (710 mg, 5.43 mmol) was added and the resulting solution was stirred for 30 min. To a solution of <strong>[74124-79-1]N,N'-disuccinimidyl carbonate</strong> (926 mg, 3.62 mmol) in dry acetonitrile (10 mL), was added 4-methylbenzyl alcohol (441 mg, 3.54 mmol) in dry CH2Cl2 (10 mL) and a catalytic amount of DMAP. The reaction mixture was stirred overnight at room temperature. The solution was then added to the amine hydrochloride previous prepared and stirred for two days at room temperature. The reaction mixture was diluted with water (15 mL) and extracted with EtOAc (4 × 15 mL). The combined organic layers were dried over MgSO4, concentrated under reduced pressure and purified by chromatography on silica gel (CH2Cl2:MeOH, 98:2) led to cis-10 as a yellow oil (466 mg, 72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With tetraethylammonium perchlorate In acetonitrile at 26℃; electrolysis; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 58% 2: 16% | With potassium 12-wolframocobalt(III)ate In water; acetic acid at 102℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium peroxydisulfate; copper diacetate In water; acetonitrile at 100℃; for 3h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dipotassium peroxodisulfate; copper diacetate; sodium acetate In acetic acid at 120℃; for 4h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With acetyl chloride In methanol at 20℃; for 3.5h; | |
84% | With methanol; [Dy2((2-hydroxy-3-methoxyphenyl)methylene benzohydrazide)2(triflate)2(H2O)4] for 24h; Reflux; Inert atmosphere; chemoselective reaction; | |
With water In acetonitrile for 0.166667h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 90% 2: 12% | With sulfuric acid at 25℃; reagents ratio; deuterium isotope effect; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With iodine for 2h; Reflux; chemoselective reaction; | 2. Typical procedure for alcohol acetylation General procedure: To a solution of benzyl alcohol (0.108 g, 1 mmol) in ethyl acetate (2 mL), iodine (0.1 mmol)was added and the mixture was heated at reflux for 2 h. When the reaction was complete(monitored by TLC), it was cooled and a saturated sodium thiosulfate solution (5 mL) was added. The reaction mixture was extracted with ethyl acetate (3x10 mL). The combined organiclayers were washed with brine, dried over anhydrous sodium sulphate and concentrated invacuo. The crude was then purified by column chromatography to give 1a in 97% yield (145mg, 0.97 mmol). |
89% | With platinum; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20 - 60℃; for 2h; Inert atmosphere; Electrochemical reaction; Green chemistry; | |
86% | With iron(III) perchlorate for 2h; Ambient temperature; |
79% | With caesium carbonate at 125℃; for 31h; | |
78% | With silica gel; iron(III) perchlorate for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With ZnAl2O4 nanoparticles at 20℃; for 0.25h; Neat (no solvent); | |
91% | With hydroxyapatite supported copper(I) oxide In acetonitrile at 50℃; for 0.0833333h; | General procedure for O-acetylation of alcohols and phenols using HAP-Cu2O General procedure: A mixture of alcohol or phenol (1 mmol), acetyl chloride(1 mmol), hydroxyapatite -Cu2O (0.1 g) in acetonitrilewas taken in a round-bottom flask and stirred at 50 °C foran appropriate time. On completion (monitored by TLC),the reaction mixture was cooled to room temperature andfiltered. The residue was washed with water followed byEtOAc (3 × 10 mL). The product was obtained after theremoval of solvent under reduced pressure followed bycrystallization from pet ether or EtOAc:pet ether or passingthrough column of silica and elution with EtOAc:pet ether. |
With acetic acid |
With pyridine In dichloromethane | ||
With pyridine In benzene Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 77.7% 2: 8.25% | With oxygen at 80℃; atmospheric pressure; | |
With H5PV2Mo10O40; lithium nitrate at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With 2,2'-(phenylimino)bis[ethanol]; diethylzinc In toluene at 20℃; for 3h; | |
87% | With 2,2'-(phenylimino)bis[ethanol]; diethylzinc In hexane; toluene at 20℃; for 3h; | |
75% | With TBA7[γ-HGeW10O36] In acetonitrile at 39.84℃; for 0.0166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.84 g (52%) | 4-Methylbenzyl 5-amino-4-oxopentanoate Hydrochloride [Compound 3] From 4-methylbenzyl alcohol (5.0 g; 41 mmol) and <strong>[5451-09-2]5-amino-4-oxopentanoic acid hydrochloride</strong> (1.0 g; 6.0 mmol). The reaction was complete after 2 days. The yield was 0.84 g (52%). 1H NMR (200 MHz; DMSO-d6): delta 2.30 (3H, s), 2.60 (2H, t, J=6.4 Hz), 2.86 (2H, t, J=6.2 Hz), 3.96 (2H, br s), 5.05 (2H, s), 7.1-7.3 (4H, m), 8.55 (3H, br s). 13C NMR (50 MHz; DMSO-d6): delta 21.7, 28.1, 35.2, 47.4, 66.4, 128.9, 129.8, 133.9, 138.2, 172.8, 203.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With 50wtpercent Cs2.5H0.5PW12O40 supported on MCM-41 In acetonitrile at 50℃; for 0.5h; | |
95% | With alum doped nanopolyaniline at 100℃; for 2h; Green chemistry; | 2.3. General procedure for acylation of alcohols and amines General procedure: In a typical reaction procedure, substituted alcohols (1.5 mmol) oramines (1.5 mmol) with acetic acid (3 mmol) were taken in to 50 mLround bottom flask and 0.037 g (0.3 mol %) of NDPANI catalyst added tothe reaction mass. The reaction was maintained at 100 C with constantstirring. The progress of the reaction was monitored by TLC. Aftercompletion of the reaction, the catalyst was recovered from the reactionmixture by simple filtration and washed several times with ethyl acetate,then dried in the oven for reuse. To remove excess acetic acid, saturatedsolution of NaHCO3 was added to the reaction mixture. The product wasextracted with chloroform and the organic layer was dried by usinganhydrous Na2SO4 and evaporated under vacuum. In few cases thecrude product was then subjected to a short silica bed with hexane andethyl acetate (8:2) mixture to eluate the corresponding acetate/amideproducts in high purity. All the products were characterized by using 1HNMR and 13C NMR spectra. |
92% | With zinc(II) oxide In neat (no solvent) at 95℃; for 2h; Green chemistry; | General procedure for esterification General procedure: To a stirred solution of carboxylic acid (5 mmol) and alcohol (5 mmol) in a 100 mL RB flask, was added 25 mg of ZnO Nps. The reaction mixture was stirred at 95 °C for 2 h and the course of the reaction was monitored by TLC. Upon completion of the reaction, the reaction mixture was filtered through a filter paper for separating the catalyst and the filtrate was quenched with ice water. The aqueous phase was extracted twice with 50 mL of dichloromethane and the organic layer was washed with 50 mL of aqueous solution of 1 M NaHCO3 followed by the 50 mL brine solution. Finally, it was dried over sodium sulfate and the required product was purified by column chromatography using silica gel to get the ester |
89% | With polyethylene glycol entrapped potassium tribromide for 0.333333h; Reflux; Green chemistry; | A representative acylation reaction was conducted by adding PEG·KBr3 (1mmol, 4.3g) to the stirred reaction mixture of alcohol (1mmol) and acetic acid (5mL). The mixture was refluxed for ca. half an hour with the progress of the reaction monitored by TLC (10% ethyl acetate/hexane). After completion of the reaction, the entire mixture was poured into a saturated solution of NaHCO3 (20mL). The product was extracted with 5mL of ethyl acetate and dried with anhydrous sodium sulphate and evaporated under vacuum to obtain the pure product. |
88% | With zinc(II) oxide for 3h; Reflux; | Acetylation of alcohols General procedure: To a mixture of acetic acid (5 mL) and alcohol (1 mmol), ZnO nanopowder (0.05 mmol) was added. The mixture was stirred vigorously under reflux conditions for 3 hr. The reaction was monitored by TLC (CCl4: EtOAc, 4:1). Then, the reaction mixture was washed with an aqueous solution of sodium bicarbonate (20%) and filtered. The filtrate was extracted with ether (3 × 50 mL), washed with H2O (3× 10 mL) and dried over anhydrous magnesium sulfate. Evaporation of solvent under reduced pressure gave the desired acetate in specified yield (Table I). All the acetates were known and characterized according to their IR, 13C and 1H NMR spectra. |
85% | With tungstophosphoric acid-modified zirconia In toluene at 110℃; for 14h; | Catalytic test General procedure: testIn all the reactions, a 25 cm3round-bottomed flask, at thereaction temperature and connected with a water jacketed con-denser, was used. In a typical experience, the reactor was loadedwith a mixture of 1 mmol of 2-phenylethanol (122 mg), 5 mmolof acetic acid (300 mg), 5 cm3of toluene and 100 mg of the cata-lyst. The mixture was stirred at 700 rpm. Samples were withdrawnfrom the organic phase at different intervals (1, 3, 5, 7, 10 and14 h). Each sample volume was approximately 10 mm3and wasdiluted with 2 cm3of acetonitrile. The concentration of substrateswas calculated with the corresponding areas, using a ShimadzuHP2010 gas chromatography instrument (Chromopack CP Sil 8 CB,30 m × 0.32 mm ID). A similar procedure was followed with theother studied alcohols and phenols.After 14 h of reaction, the solution was concentrated undervacuum, and the residue was purified by column chromatogra-phy employing silica gel as the stationary phase and a mixtureof hexane-ethyl acetate as the elution solvent. The reaction prod-ucts were identified by chromatographic comparison with standardsamples. The conversion was expressed as the ratio of moles ofproducts to moles of initial alcohol. |
71% | With S4B15W12.5 borated zirconia modified with ammonium metatungstate In toluene at 110℃; for 14h; | |
35% | With borated zirconia In toluene at 110℃; for 14h; | |
90 %Chromat. | With silver nanoparticle embedded mesoporous polyaniline nanocomposite at 100℃; for 3h; | |
83 %Chromat. | With 4,4'‑trimethylene‑N,N‑dipiperidinium sulfate In cyclohexane at 75℃; for 4h; | Typical Esterification Procedure General procedure: Glacial acetic acid (0.600 g, 0.572 mL, 10 mmol), n-butanol (9.694 g, 11.968 mL, 13 mmol), [TMDPH2][SO4] (0.308 g,1.0 mmol), and cyclohexane (1.157 g, 15 mL) were taken into a 25mL three necked flask. The flask was equipped with a manifold and a condenser. After an appropriate reaction time (4 h), a liquid bi-phase formed in the flask. The liquid phase containing the ester was isolated by separating funnel and was analysed by GC-MS. [TMDPH2][SO4] was isolated after removing theproduct and water by separating funnel and drying in a vacuumoven at 508 C overnight before being tested for reusability. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With 1,1'-bis-(diphenylphosphino)ferrocene; ruthenium(III) chloride trihydrate; In chlorobenzene; at 145℃; for 15h;Inert atmosphere; | An oven-dried 10 mL reaction vessel was charged with RuCl3·3H2O (2.6 mg, 0.01 mmol), dppf (5.6 mg, 0.01 mmol), 2 (0.6 mmol), and purged with argon three times. 1 (0.2 mmol) and chlorobenzene (0.8 mL) were added to the sealed reaction vessel by a syringe. The resulting solution was stirred at 145 C for 15 h. After cooling to room temperature, the volatiles were removed under vacuum and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate) to give 3. All new compounds were characterized by means of 1H NMR, 13C NMR, MS (EI) and HR-MS. Compound 3a: 1H NMR (400 MHz, CDCl3, ppm) delta 7.22 (d, J = 7.7 Hz, 2H), 7.12 (d, J = 7.7 Hz, 2H), 3.53 (s, 2H), 2.41 (t, J = 7.3 Hz, 4H), 2.35 (s, 3H), 1.46 (quintet, J = 7.3 Hz, 4H), 1.31 (sextet, J = 7.3 Hz, 4H), 0.90 (t, J = 7.3 Hz, 6H); 13C NMR (100 MHz, CDCl3, ppm) delta 137.1, 136.0, 128.8, 128.7, 58.4, 53.6, 29.3, 21.1, 20.6, 14.0; MS (EI) m/z (%) 233, 190, 105 (100), 77; HR-MS calcd for: C16H28N [M+H]+ 234.2216, found 234.2212. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 2h; | A typical synthetic procedure is as follows. 1,7-dibromo perylene diimide (1, 77 mg, 0.1 mmol) was dissolved into 5 mL of dimethylformamide (DMF). To which alkyl alcohol (R-OH, 0.5 mmol) and potassium carbonate (K2CO3, 70 mg, 0.5 mmol) were added. The resulted mixture was then allowed reacted under 80C for 1-4 hours. The reaction mixture was then powered into 15 mL water and the red solid was then re-dissolved in 20 mL dichloromethane (DCM) and washed with 1N hydrochloric acid and then water each for 3 times. Then, DCM layer was dried over Na2SO4. After removal of DCM, the residue was applied to chromatography with CH2Cl2/ethyl acetate (100:0-100:2) as eluents to afford the desired products 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With caesium carbonate at 125℃; for 31h; |
Yield | Reaction Conditions | Operation in experiment |
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52% | With di-tert-butyl peroxide; copper(l) chloride; at 120℃; for 6h; | General procedure: 2'-Bromoacetophenone (1a) (100.0 mg, 0.5mmol), benzyl alcohol (5a) (325.0mg,1.5mmol), CuCl (5.0mg, 0.05mmol), DTBP (365.0mg, 1.25 mmol), and 25% aqueous ammonia (0.5 mL) were placed in a thick-walled Pyrex screw-captube(25mL), and the tube was capped and the mixture heated in an oil bath at 120 C with stirring for 6 h. After the reaction mixture was cooled to room temperature, the workup and isolation of the products were essentially similar to the procedure above-mentioned. Compound 3a was obtained as white solid in 65% (71.5 mg, 0.33 mmol), and the GC analysis of the reaction mixture disclosed the formation of 3a in 66% GC yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With chlorocarbonylbis(triphenylphosphine)rhodium(I); potassium hydroxide; In 1,4-dioxane; at 95℃; for 9h; | General procedure: Ketones (1 mmol), alcohols (1.5 mmol), RhCl(CO)(PPh3)2 (2 mol%) and bases (2mmol) were added into dioxane (3 mL). The reaction mixture was stirred at 95 forcompletion monitored by TLC. Then the solution was filtered by suction and the solventwas evaporated under reduced pressure. The residue was passed through flash columnchromatography on silica gel to give the pure products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With C41H36AsClN3OPRuS; potassium hydroxide; In toluene; at 100℃; for 12h; | General procedure: Amine/sulfonamide (1mmol), alcohol (1mmol), catalyst (0.5mol %), KOH (50mol %) and toluene (2mL) were placed in a 25mL round bottomed flask and stirred on a preheated oil bath (100C) for 12h. Upon completion (as monitored by TLC), the reaction mixture was cooled at ambient temperature, H2O (3mL) was added and the organic layer was extracted with CH2Cl2. The organic extract was separated, dried, and concentrated. The desired product was purified by column chromatography with n-hexane/EtOAc as eluent. |
90% | With C51H40Cl2N2O3P2Ru; potassium hydroxide; In toluene; at 120℃; for 14h; | General procedure: 0.5 mol% ruthenium(II) catalyst was stirred with 4 mmol ofKOH in toluene. To this mixture, 2 mmol of alcohol and 2 mmolof amine were added and the temperature was raised up to120 C. The progress of the reactions was monitored using TLC.As soon as the reaction was completed, the mixture was cooledto room temperature and added 3 mL of distilled water. The combinedmixture was extracted with CH2Cl2 and dried by addingmagnesium sulfate. The crude product was purified by columnchromatography (n-hexane/EtOAc) and characterized by 1H NMRspectral analyses. The 1H NMR data obtained for the catalytic productswere compared with literature [19]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With platinum; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20 - 60℃; for 2h; Inert atmosphere; Electrochemical reaction; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
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17.2% | With potassium tert-butylate; In tert-butyl alcohol; for 24.0h;Reflux; | Step 1 : 5-Fluoro-2-(4-methylbenzyloxy)pyrimidin-4-amine. To a magnetically stirred mixture of <strong>[155-10-2]4-amino-2-chloro-5-fluoropyrimidine</strong> (11.10 grams (g), 75.2 millimoles (mmol)) in p-4- methylbenzyl alcohol (11.70 g, 82.8 mmol) was added potassium tert-butoxide in tert-butyl alcohol (KO'Bu, 1.0 M solution in 'BuOH; 82.8 milliliters (mL), 82.8 mmol) in one portion, and the resulting tan mixture was heated to reflux and stirred for 24 hours (h). The solvent was removed in vacuo and the resulting red-orange oil was purified by flash chromatography (Si02, 0?10% methyl alcohol (CH3OH) in dichloromethane (CH2C12) to give 5.5 g of red-orange oil. The oil was suspended in hexanes (100 mL) and stirred for 16 h. Water (100 mL) was added to the unchanged mixture, and the biphasic system was stirred vigorously for 1 h. The resulting cream colored solid was collected by vacuum filtration, washed with warm water (55 C, 2 x 100 mL), and dried under vacuum at 55 C for 16 h to give 5-fluoro-2-(4- methylbenzyloxy)pyrimidin-4-amine (3.30 g, 17.2% yield) as a white solid: mp 111-112 C; 1H NMR (300MHz, CDC13) delta 7.84 (d, J= 2.6 Hz, 1H), 7.42-7.38 (m, 2H), 7.03-6.97 (m, 2H), 5.99 (q, J= 6.6 Hz, 1H), 5.09 (br s, 2H), 1.61 (d, J= 6.6 Hz, 3H); MS (ESI) m/z 252 (M+H)+, m/z 250 (M-H)~. |
50.8 g | A 500-mL round bottomed flask is equipped with overhead stirring and a 22 tray X 1? Oldershaw column. To the flask is added tert-amyl alcohol (245 grams (g), 2.78 moles (mol),7.9 equivalents (eq) based on CFAP), 4-methylbenzyl alcohol (63 g, 0.52 mol, 1.5 eq based on CFAP), and flake KOH (90%; 31.1 g 0.5 mol, 1.5 eq based on CFAP). The mixture is stirred and heated to boiling. The system is held at total reflux for about 30 minutes (mm) to equilibrate the Oldershaw colunm, after which distillation is begun with a reflux ratio of 20:1. After about 8.5 hours (h), Karl Fisher titration of the bottoms indicates about 0.82% water. Heating isstopped. Once the mixture reaches room temperature, CFAP is added (49.6 g, 0.34 mol). The mixture is heated to and held at about 80-90 C and sampled periodically for high-performance liquid chromatography (HPLC) analysis. After 10.75 h at reaction temperature, CFAP is <0.5% by area and heating is stopped. Once the mixture reaches 65 C, water (124.6 g) is added, which cools the mixture to about 48 C. The mixture is stirred while warming it back to about 65 C.The warm mixture is transferred to a separatory funnel. The brine layer is cut, and the organic layer (that includes a small rag layer) is returned to the distillation flask. To the stirring organic layer is added an additional water wash (about 124.6 g), and the mixture is warmed to 65 C, transferred to a separatory funnel, and left overnight for phase separation. During the cooling period, Compound 1 crystallizes in the organic phase. The aqueous phase is cut, and the organic phase containing the crystals is heated to dissolve the solids and enable easier removal from the separatory funnel. The organic phase (about 225 g) is transferred to a flask and concentrated by rotary evaporation to about 129.1 g. As the product begins to precipitate during theconcentration, vacuum is discontinued and the rotary evaporator bath is heated to about 75 C to re-dissolve the solids. The flask is removed from the rotary evaporator, overhead stirring is added, and the flask is wrapped with insulation to allow for a more gradual cool down period. Once the mixture had reached room temperature, the solids are isolated by filtration. The wet cake (about 63.1 g) is washed with cold tert-amyl alcohol (58.9 g), and the washed cake is driedin the fume hood. HPLC internal standard analysis is carried out on the dried solid (50.8 g,98.5% Compound 1, 0.21 mol), the mother liquor (48.7 g, 23.9% Compound 1, 0.05 mol), and the cake wash (62.3 g, 11.2% Compound 1, 0.03 mol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With dipotassium peroxodisulfate; iron(III) chloride hexahydrate; In water; dimethyl sulfoxide; at 100℃; for 12h; | A dried reflux tube equipped witha magnetic stir bar charged with benzothiazole derivative (0.5 mmol 1.0equiv), benzylalcohol derivative (1.5mmol 3.0equiv), FeCl3·6H2O (0.1equiv), K2S2O8 (2.0 equiv), DMSO/H2O (2:1 mL) and the reaction vessel was placedin a 100C oil bath for 12 h under air. After cooling to room temperature,the mixture was diluted with ethyl acetate and directly filtered through a padof celite and washed with water. The organic phase was dried over NaSO4and removed under reduced vacuum. The residue was purified by columnchromatography eluting with ethyl acetate and hexane to afford thedesired product. |
37% | With tert.-butylhydroperoxide; copper dichloride; In water; at 80℃; for 24.5h;Inert atmosphere; Schlenk technique; | General procedure: A 25 mL reaction vessel was charged with benzothiazole 1 (1.86 mmol, 1.1 equiv), benzylic alcohol 4 (1.69 mmol), CuCl2 (0.51 mmol, 0.3 equiv), and tert-butyl hydroperoxide (4.06mmol, 2.4equiv, 70% aqueous solution) under nitrogen. The reaction mixture was stirred in an ice bath for 30 min, and then stirred at 80C for 24 h. After cooling to room temperature, the mixture was purified by column chromatography using silica gel (petroleum ether/ethyl acetate) to afford the products 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate; In acetone; for 6h;Reflux; | General procedure: <strong>[3470-50-6]6-Hydroxy-1-tetralone</strong> (0.3 g, 1.85 mmol) was suspended in acetone (15 mL) containing K2CO3 (3.70 mmol). The reaction was treated with an appropriately substituted arylalkyl bromide (2.035 mmol) and heated under reflux for 6 h. The reaction progress was monitored using silica gel TLC with ethyl acetate:petroleum ether (1:2) as mobile phase. Upon completion, the reaction was filtered through a pad of celite and concentrated in vacuo. The crude thus obtained was purified by recrystallization from cyclohexane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With tert.-butylhydroperoxide; copper(II) acetate monohydrate; calcium carbonate; In acetonitrile; at 80℃; for 24h; | General procedure: An oven-dried 15 mL glass vial with a magnetic stirrer bar was charged with Cu(OAc)2·H2O (12 mg, 6 mol%), N,O-dimethylhydroxylamine hydrochloride (2; 117 mg, 1.2 mmol), the respective benzyl alcohol 1 (1 mmol), aq 70% TBHP (0.17 mL, 1.2 mmol), CaCO3 (120 mg, 1.2 mmol) in MeCN (1 mL). The glass vial was flushed with N2 three times and the contents were stirred at r.t. for 1 h. Then the reaction mixture was stirred for 24 h at 80 C. After completion of the reaction, the mixture was cooled to r.t. All volatiles were removed under vacuum. The product was extracted with EtOAc (20 mL) and the organic layer was washed with sat. aq NaHCO3 (20 mL), dried (Na2SO4), and the solvent removed under vacuum. The Weinreb amide product 3 was purified by column chromatography (silica gel, 100-200 mesh) using a gradient of petroleum ether (bp 60-80 C) and EtOAc. All the amides were identified by GC-MS, 1H, and 13C NMR spectroscopic analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With sodium t-butanolate In toluene at 100℃; for 65h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With sodium t-butanolate In toluene at 100℃; for 65h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium t-butanolate In toluene at 100℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium hydroxide; In toluene; at 90℃; for 20h; | General procedure: To an oven-dried 20 cm3 test tube with a ground-in stopperequipped with a stir bar were added anthranilamide (1.0 mmol), benzyl alcohol (1.0 mmol), KOH (2.0 mmol),and 4 cm3 toluene. The test tube was put in an oil bath potpreheated at 90 C and the mixture was stirred for 20 h at90 C. After cooling to room temperature, the reactionmixture was added about 5 g silica gel and directly condensedon a rotator under vacuum. The resulting residualwas transferred to a silica gel chromatography column andeluted with a solution of petroleum ether and ethyl acetate[4/1 (v/v)] to give a white solid 2-phenyl-4(3H)-quinazolinone.For some products (3f, 3g, 3n, and 3t) onlysparingly soluble in ethyl acetate, the reaction mixtureswere condensed in vacuo on a rotary evaporator. Theresiduals were washed three times with water and oncewith ethyl acetate, and then dried in an infrared oven togive the desired products pure enough for NMR analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With tetrabutylammonium bromide; In N,N-dimethyl-formamide; at 80℃; for 1.83333h; | General procedure: A mixture of alcohol (1 mmol), 1,2-phenylenediamine or 2-aminothiophenol(1 mmol), Pd(II)Cl2-BTPMNPs (0.019 g, containing 0.09mol% Pd) and (1 mmol) tetrabutylammonium bromide (TBAB, 0.01 g)in DMF (5 mL) in a round-bottomed flask equipped with a condenser wasstirred at 80 C. The progress of the reaction was monitored by TLC(eluent: n-Hexane/EtOAc, 4: 1 for benzimidazoles and n-Hexane/EtOAc, 6: 1 for benzothiazoles). The catalyst was separated by permanentmagnet and washed with EtOAc (10 mL). The crude product waspurified by recrystallization from EtOAc or EtOH to afford the purebenzimidazole. The benzothiazoles was obtained by recrystallizationfrom n-hexane/EtOAc (10: 1). |
79% | With anhydrous sodium carbonate; In neat (no solvent); at 120℃;Green chemistry; | General procedure: Typically, o-phenylenediamine (1.3 mmol) or 2-aminothiophenol (1 mmol), benzyl alcohols (1 mmol), Na2CO3 (20 mol%), and Pd-NPs/Cu2(BDC)2(DABCO) (20 mg, 0.01 mol%) were added to a round-bottom flask. The reaction mixture was heated to 120 Cand stirred at for the appropriate time in air (TLC monitoring). Ethyl acetate was added to the reaction mixture and catalyst was filtered. For the purification of impure products, chromatography on silica gel was performed (EtOAc:Hep. (1:6)). The entire products characterized by melting point, CHN, 1H-NMR and13C-NMR spectroscopy. |
79% | With potassium-t-butoxide; In toluene; at 20 - 110℃; for 48h; | At room temperature, add o-aminothiophenol 1a (0.6 mmol), toluene solvent and 4-methylbenzyl alcohol 2e (0.2 mmol) to the reactor in turn, stir at room temperature to fully dissolve them, and add to Example 1 in turn The prepared HKUST-1-400 catalyst (20mg), potassium tert-butoxide (0.2mmol), after dissolving, continue the reaction and place it at 110C for 2 days. After the completion of the reaction is detected by TLC, the Cu-MOF derivative material is filtered out first The HKUST-1-400 catalyst was then subjected to column chromatography to obtain the target compound 3e with a yield of 79%. |
73% | With [Pd(COD)Cl(SnCl3)]; In o-dimethylbenzene; at 140℃; for 24h; | General procedure: A mixture of aniline 1 (23.28 mg, 0.25 mmol), benzyl alcohol 2 (27 mg, 0.25 mmol), [Pd(COD)Cl(SnCl3)] (3.5 mg, 0.007 mmol) in 3mL of o-xylene was stirred at 140 C for 24h. Then, solvent was removed under reduced pressure, and the mixture was subjected to column chromatography over silica gel (100-200 mesh, eluent: petroleum ether 60-80 C/ethylacetate 20:1 v/v) to afford a corresponding product 3 as a yellow color oil in 90% (41.5 mg) isolated yield. |
With oxygen; In acetonitrile; under 760.051 Torr; for 10h;Schlenk technique; Sealed tube; Irradiation; Green chemistry; | General procedure: The synthesis of 2-substituted benzothiazoles from oaminothiophenols and alcohols was performed in a sealed Schlenk tube under visible light irradiation. Typically, a mixture of oaminothiophenol(0.1 mmol) and alcohol (0.3 mmol) in acetonitrile(CH3CN, 2 mL) was saturated with O2 before the mixture wastransferred into a 10 mL tube containing 10 mg of MOFs. The suspensionwas irradiated with a 300WXe lamp equipped with a UVcutfilter to remove all irradiations with wavelengths less than420 nm and an IR-cut filter to remove all irradiations with wavelengthsgreater than 800 nm. After the reaction, the suspensionwas filtered through a porous membrane (diameter 20 μm) andthe products were analyzed by GC-MS and GC-FID (ShimadzuGC-2014) with an HP-5 capillary column. The reaction, scaled upby 10 times, was conducted under similar conditions in a homemadereactor. A mixture of o-aminothiophenol (1 mmol) and benzylalcohol (3 mmol) in CH3CN (20 ml) saturated with O2 wastransferred to the homemade reactor containing 100 mg of MIL-100(Fe). The reactor was irradiated with a 300W Xe lampequipped with both a UV-cut filter and an IR-cut filter. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With potassium <i>tert</i>-butylate In 1,4-dioxane at 120℃; for 53h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 20℃; for 15h; | (1) To a solution of methyl 4-imidazole carboxylate (a-1) (3.0 g, 24 mmol) in THF (60 mL), p-methylbenzyl alcohol (a-15) (2.9 g, 24 mmol) and PPh3 (16 g, 60 mmol) were added and after adding a toluene solution (32 mL, 60 mmol) of 1.9 mol/L DIAD dropwise, the resulting mixture was stirred at room temperature for 15 hours. After distilling off the solvents under reduced pressure, purification was performed by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give methyl 1-(4-methylbenzyl)-1H-imidazole-5-carboxylate (a-16) (amount, 4.3 g; yield, 78%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With Cu/OMS-2; In toluene; at 90.0℃; for 20.0h; | General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | A thermometer in 100 mL 3-neck flask and stirred insert the dichloromethane 20 mL and using an ice-bath the inner temperature of 0 to 5C. Here sodium para-toluene sulfonate, 388.4 mg (2.0 mmole) and bis (trichloromethyl) carbonate, 236mg (0.80 mmole, 0.40 molbae) and tribasic monohydrate, potassium (K3PO4*H 2O) 1.38g (6 Mmole, 3 moles) were added in this order and stirred for 5 minutes.It is observed that when two drops of triethylamine (about 20 mg, 0.10 mole ratio) are added thereto, bubbles are generated in the reactor.After that, the ice-bath is removed and the temperature is raised to room temperature. The mixture is further stirred for 20 minutes.The reaction was completed by TLC analysis when 244.3 mg (2.0 mmole) of 4-methylbenzyl alcohol, 202.4 mg (2.0 mmole) of triethylamine and 13.1 mg (0.2 mmole) of trimethylamine hydrochloride were sequentially added and stirred at room temperature for 30 minutes You can check.After confirming the completion of the reaction, the reaction mixture was filtered and washed with dichloromethane (10 mL) to remove insoluble salts. The resulting solution was distilled under reduced pressure to obtain 519 mg of a target compound, a tosylate derivative (yield 94%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tert.-butylhydroperoxide; tetrabutyl phosphonium bromide; In water; chlorobenzene; at 80℃; for 2.5h;Sealed tube; | General procedure: In a 5 mL sealed tube, TBPB(30 mol%, 0.041 g), and TBHP (70 wt% in H2O, 1.0 mmol, 0.131 g) was added to a solution ofbenzyl alcohol 1a (0.4 mmol, 0.043 g) in chlorobenzene (1 mL). The resultant mixture washeated at 80 C for 2.5 h. After completion of the reaction as was indicated by TLC monitoring,the reaction mixture was cooled to ambient temperature and saturated NaHCO3 (2 mL) wasadded. The product was extracted with ethyl acetate (2 × 3 mL). The combined organic phasewas dried over Na2SO4. The solvent was removed under the reduced pressure. The residue waspurified by column chromatography using n-hexane-EtOAc (15:1) as eluent to afford pureproduct 2a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With C50H41ClIrNOP2; potassium hydroxide; In 1,4-dioxane; at 100℃; for 24h;Schlenk technique; Inert atmosphere; | under high purity nitrogen atmosphere, into a 10ml reaction tube was added Schlek 0.01mmol benzoquinoline ring iridium hydrogen triphenylphosphine adduct (3), 1 mmol of phenylacetylene, 1.5mmol p-methylbenzyl alcohol, 0.5mmol of potassium hydroxide and 3ml of dioxane, the reaction tube was replaced by nitrogen three times, and then in an oil bath with magnetic stirring and heated to 100 deg.] C, The reaction was refluxed for 24 hours. Oil bath was removed, the water bath to room temperature; 3ml adding water to the reaction liquid, extracted three times with 5ml of dichloromethane, and the combined organic phases were dried over anhydrous MgSO4 for 30 minutes and filtered; the filtrate was concentrated on a rotary evaporator, the remaining oil residue ether as eluent, separated by thin layer chromatography on silica gel to give the pure product 1- methyl-3-phenyl-1-propanone, a yield of 93%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | General procedure: To a solution of benzyl alcohol (1 mmol) in MeCN (10 mL) was added PhI(OAc)2 (1 mmol) and the reaction was stirred for 10 min. Then NHSI (1.5 mmol) was added and stirring was continued for 15 min. To this mixture, amino acid ester (1 mmol) was added under nitrogen atmosphere. The reaction was stirred for 1-2 h at room temperature till the completion of reaction (consumption of NHSI ester by TLC analysis). The reaction mixture was quenched with water and extracted with EtOAc. (10 mL 3). The combined organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (n-hexane-EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.9% | With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,4-di(diphenylphosphino)-butane; bis-[(trifluoroacetoxy)iodo]benzene; In N,N-dimethyl-formamide; at 90℃; for 9h; | To a solution of N, N-dimethylformamide (DMF) in a volume ratio of 4: 1 with polyethylene glycol 200(PEG-200)) was added 100 mmol of the compound of the above formula (I), 70 mmol of the compound of the above formula (II), 10 mmol of catalyst bis (triphenylphosphine) cyclopentadienyl ruthenium chloride,(TDI) 2), 12 mmol of organic ligand L1 and 70 mmol of base, 5,7-triazabicyclo [4.4.0] dec-5-ene (TBD), Then stirred to a temperature of 90 C, and the reaction was stirred at that temperature for 9 hours;After completion of the reaction, the reaction system is naturally cooled to room temperature and the pH is adjusted to neutral, filtered and the filtrate is saturatedSalt water washing, and then extracted with ethyl acetate 2-3 times,The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with a 1: 2 by volume mixture of chloroform and petroleum ether to give the compound of formula (III) Was 93.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 4-Methylbenzyl bromide; at 130℃; for 12h;Green chemistry; | <strong>[4214-79-3]2-hydroxy-5-chloropyridine</strong> (0.259 g, 2 mmol), 4-methylbenzyl alcohol(2.4 mmol, 1.2 equiv.) And 4-methylbenzyl bromide (0.0559 ml, 20 molpercent)were added successively to a tubular reactor,, Sealed directly in air, and thenheated to 130 ° C for 12 h undersolvent-freeconditions.After the TLC monitoring reaction was complete, the product was purified by column chromatography and the yield was91percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 4-Methylbenzyl bromide; at 130℃; for 24h;Green chemistry; | 4-methylbenzyl alcohol(2.4 mmol, 1.2 equiv.) And 4-methylbenzyl bromide (0.0559 ml, 20 mol%)were added in a tubular reactor to a solution of 4-methyl-2-hydroxypyridine (0.218 g,), Sealed directly in air, and thenheated to 130 C for 24 h undersolvent-freeconditions.After the TLC monitoring reaction was complete, the product was purified by column chromatography and the yield was97% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With triethylamine; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere; | A 50 ml three-necked flask equipped with a stirring reflux device was charged with 1 mmol of 2-diphenylphosphineaniline,1.1 mmol of p-methylbenzyl alcohol, 1 mmol of 2-diphenylphosphinophenyl ether, 1 mmol of RuCl2 (PPh3) 3, 1.4 mmol of triethylamine and 20 ml of dioxane were added and the mixture was heated at 110 C for 12 h under a nitrogen atmosphere.After cooling and filtering, the resulting solid was recrystallized from a mixed solvent of CH 2 Cl 2 and petroleum ether to give product 14 in a yield of 86%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32%; 20%; 28% | With tetrabutyl phosphonium bromide; Trimethylacetic acid; In water; chlorobenzene; at 80℃; for 2.5h;Sealed tube; | General procedure: In a 5 mL sealed tube, TBPB(30 mol%, 0.041 g), and TBHP (70 wt% in H2O, 1.0 mmol, 0.131 g) was added to a solution ofbenzyl alcohol 1a (0.4 mmol, 0.043 g) in chlorobenzene (1 mL). The resultant mixture washeated at 80 C for 2.5 h. After completion of the reaction as was indicated by TLC monitoring,the reaction mixture was cooled to ambient temperature and saturated NaHCO3 (2 mL) wasadded. The product was extracted with ethyl acetate (2 × 3 mL). The combined organic phasewas dried over Na2SO4. The solvent was removed under the reduced pressure. The residue waspurified by column chromatography using n-hexane-EtOAc (15:1) as eluent to afford pureproduct 2a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33%; 15%; 18% | With tetrabutyl phosphonium bromide; Trimethylacetic acid; In water; chlorobenzene; at 80℃; for 2.5h;Sealed tube; | General procedure: In a 5 mL sealed tube, TBPB(30 mol%, 0.041 g), and TBHP (70 wt% in H2O, 1.0 mmol, 0.131 g) was added to a solution ofbenzyl alcohol 1a (0.4 mmol, 0.043 g) in chlorobenzene (1 mL). The resultant mixture washeated at 80 C for 2.5 h. After completion of the reaction as was indicated by TLC monitoring,the reaction mixture was cooled to ambient temperature and saturated NaHCO3 (2 mL) wasadded. The product was extracted with ethyl acetate (2 × 3 mL). The combined organic phasewas dried over Na2SO4. The solvent was removed under the reduced pressure. The residue waspurified by column chromatography using n-hexane-EtOAc (15:1) as eluent to afford pureproduct 2a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22%; 29%; 25% | With tetrabutyl phosphonium bromide; Trimethylacetic acid; In water; chlorobenzene; at 80℃; for 2.5h;Sealed tube; | General procedure: In a 5 mL sealed tube, TBPB(30 mol%, 0.041 g), and TBHP (70 wt% in H2O, 1.0 mmol, 0.131 g) was added to a solution ofbenzyl alcohol 1a (0.4 mmol, 0.043 g) in chlorobenzene (1 mL). The resultant mixture washeated at 80 C for 2.5 h. After completion of the reaction as was indicated by TLC monitoring,the reaction mixture was cooled to ambient temperature and saturated NaHCO3 (2 mL) wasadded. The product was extracted with ethyl acetate (2 × 3 mL). The combined organic phasewas dried over Na2SO4. The solvent was removed under the reduced pressure. The residue waspurified by column chromatography using n-hexane-EtOAc (15:1) as eluent to afford pureproduct 2a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydroxide; copper(ll) bromide; In formamide; acetonitrile; at 65℃; for 24h;Schlenk technique; | General procedure: Alcohol (1 mmol), phosphonium salt (1.1 mmol), NaOH (1.1 mmol),CuBr2 (5 mol%), 2,2?-bipy (5 mol%), and TEMPO (5 mol%) were mixed in MeCN and HCONH2 (1:1, 2 mL) in a 100-mL Schlenk tube with an air balloon, and the mixture was stirred at 65 C for 24 h (monitoring by TLC and/or GC-MS). After completion, product was purified by column chromatography (EtOAc and petroleum ether). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.8% | 4-hydroxy-3-methoxyphenylacetic acid was weighed according to a molar ratio of 1:1:1.5:0.1.4-methylbenzyl alcohol, dicyclohexylcarbodiimide and 4-dimethylaminopyridine,First add 4-hydroxy-3-methoxyphenylacetic acid and 4-methylbenzyl alcohol to a three-necked flask.And add dichloroethane, stir and mix, then heat to 55 C,Subsequently, dicyclohexylcarbodiimide and 4-dimethylaminopyridine were added, and the reaction was stirred for 4 h;After the reaction is completed, dichloroethane is distilled off under reduced pressure, and the reactant is added to water, stirred and mixed, and then allowed to stand for separation, the oil phase is collected, and the oil phase is dried in an oven.The dried oil phase is mixed with a mass ratio of 1:10 and tetrahydrofuran, mixed, placed in an ice water bath, and sodium borohydride is added in an amount of 3% by mass of the oil phase, and the reaction is carried out under a nitrogen atmosphere for 2 hours.After the reaction, tetrahydrofuran is recovered, and the reaction liquid is added to water, and filtered with suction to obtain a residue, washed, and dried.After recrystallization, you can get1-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)propan-2-one,The purity was 95.2%, and the yield was 96.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With air; at 80℃; for 24h;Sealed tube; High pressure; Alkaline conditions; | 2-amino-4-methylbenzonitrile (132.2 mg, 1.0 mmol), 4-methylbenzyl alcohol (146.6 mg, 1.2 mmol, 1.2 equiv.), cesium hydroxide monohydrate, were sequentially added to a 100 mL high pressure sealed tube. (167.9 mg, 1.0 mmol), an air balloon was added to the sealed tube, and stirred at 80 C for 24 h. After the reaction was completely monitored by TLC or GC-MS, the product was purified by column chromatography. The isolated yield was 95%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With C15H25Cl2N3NiO3; potassium <i>tert</i>-butylate In toluene at 110℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With MnBr(CO)2[NH(CH2CH2P(Cy)2)2]; potassium <i>tert</i>-butylate In toluene at 80℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium azide; dihydrogen peroxide In ethanol at 78℃; | 2.3 General Procedure for Synthesis of 4-aryl-NH-1, 2, 3-triazoles General procedure: A round-bottomed flask (10 mL) was charged with benzyl alcohol (1.0 mmol), sodium azide (2.0 mmol), H2O2(3 mmol) and nitromethane (2.0 mmol) were added in ethanol (4 mL). Afterwards, the mixture was refluxed in the presence of 40 mg Fe3O4SiO2TCT-DABCO-SO3H magnetic catalyst. After completion of the reaction, the magnetic catalyst was separated by using an external magnet, finally, the product had to be isolated by column chromatography on silica gel (70-230 Mesh) using n-hexane-ethyl (4:1) acetate as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With C15H25Cl2N3NiO3; potassium <i>tert</i>-butylate In octane at 120℃; for 24h; Schlenk technique; Inert atmosphere; |
Tags: 589-18-4 synthesis path| 589-18-4 SDS| 589-18-4 COA| 589-18-4 purity| 589-18-4 application| 589-18-4 NMR| 589-18-4 COA| 589-18-4 structure
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Code | Phrase |
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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