| 99% |
With bismuth(lll) trifluoromethanesulfonate In acetonitrile at 20℃; for 0.0833333h; |
|
| 99% |
With tin(IV) tetraphenylporphyrin perchlorate at 20℃; for 0.0833333h; |
|
| 99% |
at 20℃; for 6h; |
|
| 99% |
With [{CpHf(OH2)3}2(μ2-OH)2][OSO2C8F17]4*4H20*2THF at 20℃; for 0.5h; |
|
| 99% |
With Cp2Ti(OSO2C8F17)2 at 20℃; for 0.0333333h; Neat (no solvent); |
|
| 99% |
With silica gel for 0.0583333h; Microwave irradiation; neat (no solvent); |
|
| 99% |
With polyvinylpolypyrrolidone-bound boron trifluoride In acetonitrile at 20℃; for 0.5h; |
|
| 99% |
With C12H8N2*2CH4O3S at 50℃; for 2h; |
|
| 99.7% |
With silica-supported platinum In 1,2-dichloro-ethane for 1h; Reflux; |
1.1-1.3; 2.1-10.1; 1-4
Step 1. 100 g of phenylethyl alcohol and 200 ml of dichloroethane.The catalyst Pt/Si022g was added to a mechanical stirring rod, and the reflux condenser was placed.In a 500 ml four-necked flask with a constant pressure funnel,While stirring, 55 g of acetic anhydride was slowly added dropwise and refluxed for 1 h;Step 2. Change the reflux device to a distillation device and distill off part of the dichloroethane.Until the distillate is clear, the amount of evaporation is 100 ml;Step 3. Cool the reaction solution to below 10 ° C and wash with ice water.A solution of phenylethyl acetate in dichloroethane is obtained, dried over anhydrous magnesium sulfate.Dichloroethane was completely distilled off under reduced pressure to give phenylethyl acetate. |
| 98% |
With vanadyl triflate In dichloromethane at 20℃; for 0.5h; |
|
| 97% |
In acetonitrile at 20℃; for 0.25h; |
|
| 97% |
With silica gel-supported phosphotungstic acid In chloroform at 20℃; for 0.0666667h; |
|
| 97% |
With N,N'-diiodo-N,N'-1,2-ethanediylbis(p-toluenesulphonamide) at 80℃; for 0.216667h; neat (no solvent); |
|
| 97% |
With Methylenediphosphonic acid at 20℃; for 2h; neat (no solvent); |
|
| 97% |
With silica-sulfuric acid nanoparticles In neat (no solvent) at 20℃; for 0.0833333h; |
|
| 97% |
With poly(N,N'-dibromo-N-ethylnaphthyl-2,7-sulfonamide) In neat (no solvent) at 20℃; for 0.133333h; |
General Procedure for acetylation of Alcohols, Phenols, Thiol and Amine with Ac2O in the presence of PBNS under solvent-free conditions
General procedure: Alcohol, phenol, thiol or amine (1 mmol) was added to a mixture of Ac2O (2 mmol) and PBNS (30 mg), and the resulting mixture was stirred at room temperature. After completion of the reaction as monitored by TLC (nhexane/acetone: 9/1), CH2Cl2 (10 mL) was added to the reaction mixture, stirred for 1 min, and the catalyst was filtered.The precipitate was washed with CH2Cl2 (210 mL) and dried to give the recycled PBNS. Water (20 mL) was added to the filtrate and decanted. The organic layer was dried over anhydrous Na2SO4. Then, the purity of the product was checked by TLC for several times, which had only one spot related to the final product; after ensuring about that, evaporation of the solvent gave the desired pure product in good yield. |
| 97% |
With (2,3,4,5,6-pentafluorophenyl)ammonium triflate In neat (no solvent) at 20℃; for 0.333333h; |
|
| 96% |
With lanthanum(III) nitrate at 20℃; for 0.333333h; |
|
| 96% |
With supported L-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate on Silica Gel at 20℃; for 1.3h; Green chemistry; |
|
| 95% |
With bismuth oxide perchlorate at 20℃; for 1h; |
|
| 95% |
With 1-hexyl-3-methylimidazolium hydrogen sulphate at 50℃; for 0.75h; Neat (no solvent); |
|
| 95% |
With multi-walled carbonnanotubes functionalized with phosphonic acid In neat (no solvent) at 20℃; for 0.166667h; |
|
| 95% |
With zirconium phosphate In neat (no solvent) at 60℃; for 0.5h; Green chemistry; |
|
| 95% |
With tetrakis(triphenylphosphineoxide)dioxouranium(VI) perchlorate In dichloromethane-d2 at 22℃; for 0.75h; |
|
| 94% |
With decamolybdodivanadogermanic acid nanoparticles at 24.84℃; for 0.075h; Neat (no solvent); |
|
| 94% |
With iron(III) p-toluenesulfonate hexahydrate In neat (no solvent) at 20℃; for 0.166667h; |
Method A (synthesis of an acetate under solvent-free conditions)
General procedure: A homogenous mixture of cinnamyl alcohol (0.998 g, 7.44 mmol) and acetic anhydride (0.987 g, 0.91 mL, 9.67 mmol) was stirred as Fe(OTs)3·6H2O (0.101 g, 0.1487 mmol, 2.0 mol %) was added. The progress of the reaction was followed by GC. After 15 min, aqueous 10% Na2CO3 (10 mL) was added and the mixture was stirred for 10 min. The reaction mixture was extracted with ethyl acetate (2 × 20 mL). The combined organic layers were washed with saturated aqueous NaCl (15 mL), dried (Na2SO4), and concentrated on a rotary evaporator to yield 1.248 g (95%) of a clear, slightly yellow liquid that was identified as cinnamyl acetate and was determined to be >98% pure by 1H & 13C NMR spectroscopy, and 96% pure by GC. |
| 94% |
With graphite oxide In dichloromethane at 20℃; for 0.0833333h; Green chemistry; |
General procedure for the acetylation of alcohols and phenols with Ac2O catalyzed by GO.
General procedure: To a solution of alcohols or phenols (3 mmol) and Ac2O (4.5 mmol; 9 mmol for dihydroxybenzenes) in CH3CN or CH2Cl2(2 mL) in a round-bottom flask was added GO (5 wt% of alcohols orphenols). The mixture was stirred at 20 °C and the progress of the reaction was monitored by thin layer chromatography (TLC) analysis. After the completion of the reaction, the catalyst was filtered and washed with ethyl acetate (20 mL x 2). The filtrate was combined and washed with 15 mL of saturated sodium carbonate. The organic phase was dried over Na2SO4 and evaporated in vacuo to obtain the desired products. To determine the catalytic activity of Mn and K, we added MnO2, MnSO4 or KCl in the reaction between2-phenylethanol with Ac2O instead of GO and the yields of the corresponding ester (determined by 1H NMR) were listed in Table S1. |
| 93% |
at 20℃; for 0.5h; |
|
| 93% |
With pyridine at 30℃; for 0.25h; |
|
| 93% |
With silica sulfate In chloroform at 20℃; for 0.05h; |
|
| 93% |
With N,N'-dibromo-N,N'-1,2-ethanediylbis-(benzenesulfonamide) at 20℃; for 5h; neat (no solvent); |
|
| 93% |
With phenyl-trimethyl-ammonium perbromide In chloroform at 20℃; for 23h; |
|
| 93% |
With lithium bis(perfluorooctylsulfonyl)amide at 30℃; for 46h; |
|
| 92% |
With melamine-N2,N4,N6-trisulfonic acid In dichloromethane at 20℃; for 0.333333h; |
|
| 92% |
In neat (no solvent) at 75℃; for 0.416667h; |
Catalytic tests
General procedure: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 °C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC-MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10% solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC-MS, FT-IR, and 1H-NMR spectral data by comparing thesespectra with those of standard samples or literature data. |
| 92% |
With sulfonic acid-functionalized hyper-cross-linked poly(2-naphthol) In neat (no solvent) at 25℃; for 0.25h; Green chemistry; chemoselective reaction; |
2.3 General Procedure forAcylation Reaction
General procedure: To a 10mL reaction flask phenol/alcohol/thiol/amine/aldehyde(1mmol), acetic anhydride (1mmol) and p2NPh-OSO3H(10mg) as a catalyst was added and the resulting mixturestirred at 25°C. The progress of the reaction was checkedusing thin layer chromatography (TLC). After completion,ethyl acetate (EA) was added and the catalyst was separatedfrom the reaction mixture by straightforward filtration. Theseparated catalyst was cleaned with EA (10mL) and then driedin an oven for 2h and reused for further reaction. The reactionmixture was evaporated under reduced pressure to get theproducts which were characterized by 1H and 13C NMR spectroscopy.All of the obtained products are renowned withinthe literature. |
| 91% |
With 5,10,15,20-tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate In acetonitrile at 20℃; for 0.00833333h; |
|
| 91% |
With 20CuO-ZnO nanocatalyst In dichloromethane at 20℃; for 0.333333h; Green chemistry; |
2.3. General procedure for the acetylation of alcohols
General procedure: A heterogenous mixture of alcohol (1 mmol), acetic anhydride (1.2 mmol) and the 20CuO-ZnO nanocatalyst (0.05g) in CH2Cl2 (10 mL) was stirred at room temperature. Upon completion of the reaction, as determined by TLC, the mixture was filtered to recover the catalyst. The catalyst was washedwith CH2Cl2 (5 mL) and then dried at X °C for Y h before beingused in consecutive runs. The combined organic layers were washed sequentially with 5% (w/v) NaHCO3 solution and water and then dried over MgSO4. The solvent was then removed in vacuo to give the crude product as a residue, which was purified by column chromatography over silica gel to afford the pure desired products in high yield. |
| 91.8% |
With 5% MoO3 modified mesoporous silica In cyclohexane at 35℃; for 0.5h; |
|
| 90% |
With Sm{N<SO2OCH(CF3)2>2}3 In dichloromethane at 30℃; for 0.833333h; |
|
| 90% |
at 20℃; for 1h; |
|
| 90% |
In hexane at 20℃; for 0.0166667h; |
|
| 90% |
With zirconium(IV) chloride at 20℃; for 0.75h; |
|
| 90% |
With perchloric acid at 20℃; for 0.5h; |
|
| 90% |
With silica-bonded N-propyl sulfamic acid at 20℃; for 0.416667h; chemoselective reaction; |
|
| 90% |
With saccharin sulfonic acid In dichloromethane for 2h; Reflux; |
|
| 90% |
With polyvinylpolypyrrolidone supported triflic acid In neat (no solvent) at 20℃; for 0.116667h; Green chemistry; |
General experimental procedure
General procedure: To a mixture of substrate (1.0 mmol) and acetic anhydride (1.0 mmol), 0.008 g PVPP.OTf (3.4 mol%) was added. The mixture was stirred at room temperature for the time indicated in Tables 2, 3 and 4. The progress of the reaction was followed by TLC or GC for aliphatic alcohols. After completion of the reaction, ethyl acetate (2 9 10 cm3) was added, and the catalyst was separated by filtration. The filtrate was washed with an aqueous solution of NaHCO3 (10%, 2 9 10 cm3) and water (2 9 10 cm3) and dried with Na2SO4. The solvent was evaporated under reduced pressure to afford the expected product. |
| 90% |
With polydopamine sulfamic acid-functionalized silica gel nanocatalyst In neat (no solvent) at 20℃; for 1h; |
2.2 General Procedure for Acylation Reaction
General procedure: A 25 mL ballon containing a magnetic stir bar was chargedwith phenol/alcohol/amine (1 mmol) and acetic anhydride(2 mmol), SiO2/PDA-SO3H (30 mg, 1 mol% H+)as catalyst.The reaction mixture was stirred at room temperature and thereaction progress was monitored on thin-layer chromatography(TLC). After completion of the reaction, the reaction mixturewas diluted with ethyl acetate and catalyst was separatedfrom reaction mixture by centrifugation. The reaction mixturewas washed with sat. NaHCO3solution (1 × 15 mL) and theproduct was extracted with ethyl acetate (3 × 10 mL) and driedover Na2SO4and evaporated under vacuum. All the obtainedproducts are well known in the literature. |
| 89.6% |
With pyridine; toluene-4-sulfonic acid In dichloromethane |
|
| 88% |
In acetonitrile at 20℃; for 0.416667h; |
|
| 86% |
|
|
| 86% |
With 1H-imidazole for 0.05h; Irradiation; microwave; |
|
| 86% |
With N,N'-dimethyl-N,N'-di(pyridin-4-yl)ferrocene-1,1'-dicarboxamide at 20℃; for 0.333333h; |
|
| 86% |
In neat (no solvent) at 20℃; for 0.416667h; Green chemistry; |
|
| 85% |
at 20℃; for 0.5h; |
|
| 85% |
In hexane at 20℃; for 0.0333333h; |
|
| 85% |
With magnesium bis(trifluoromethane solfonyl)imide at 20℃; for 0.166667h; |
|
| 85% |
With p-toluenesulfonyl chloride at 20℃; for 0.5h; neat (no solvent); |
|
| 85% |
With Fe3O4-polyethylene glycol composite magnetic nanoparticles In neat (no solvent) at 20℃; for 0.416667h; Sonication; Green chemistry; |
General procedure for acylation reaction under ultrasonic conditions
General procedure: A 10-mL balloon was charged with phenol/alcohol/amine (1mmol) and acetic anhy-dride (3mmol), with Fe 3 O 4 PEG (10mg) as catalyst. The reaction balloon was taken in the ultrasonic bath, where the level of the reaction mixture is lower than the surface of the water. Then, the mixture was sonicated under 60W of power of the ultrasonic bath at room temperature for the appropriate time, as shown in Table2. After completion of the reaction (monitored by thin-layer chromatography), the reaction mixture was diluted with ethyl acetate and the catalyst was separated from reaction mixture by an external magnet. The separated catalyst was washed with DI water and absolute ethanol several times then dried in oven and reused for further reaction. The reaction mixture was washed with sat. NaHCO 3 solution (1 × 15mL) and the product was extracted with ethyl acetate (3 × 10mL) and dried over Na 2 SO 4 and evaporated under vacuum. All the obtained products are well known in the liter-ature and were confirmed by nuclear magnetic resonance (NMR) analysis and com -parison with literature data. |
| 84% |
With pyridine at 20℃; for 12h; |
|
| 81% |
With 1H-imidazole at 20℃; for 4.5h; Green chemistry; |
In a typical procedure for the conversion of a benzyl alcohol into a benzyl acetate
General procedure: benzyl alcohol (1.0 mmol, 0.1 mL) was added to a stirred solution of imidazole (0.08 mmol 0.005 g) and acetic anhydride (2.0 mmol, 0.188 mL) at ambient temperature, and the progress of the reaction was monitored by TLC. Upon completion of the reaction (3 h), the residue was subjected to purification on a short column of silica gel, using n-hexane/ethyl acetate (10:1) as the eluent, to give the desired benzyl acetate as colorless liquid (0.14 g, 94% yield). 1H NMR (400 MHz, CDCl3): δ 2.13 (s, 3H), 5.14 (s, 2H), 7.29-7.43 (m, 5H). |
| 70% |
Stage #1: 2-phenylethanol With manganese(II) iodide; naphthalene; lithium In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: acetic anhydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; |
Phenyl 3-Chlorobenzoate (1c); Typical Procedure
General procedure: A 25 mL flask was charged with lithium (0.07 g, 9.68 mmol),naphthalene (0.19 g, 1.48 mmol), anhyd MnI2 (1.45 g, 4.71 mmol), and freshly distilled THF (10 mL) under argon pressure,and the mixture was stirred for 1 h at r.t. To the resultingslurry, containing 2.5 mmol of highly active manganese, wasadded PhOH (0.47 g, 5.0 mmol) and the resulting mixture wasstirred at r.t. for 10 min. Neat 3-chlorobenzoyl chloride (0.88 g,5.0 mmol) was then added to the flask, and the mixture wasstirred at r.t. for 30 min. The reaction was then quenched with3 M aq HCl, and the mixture was extracted with Et2O (3 × 10 mL).The organic layers were combined and washed with sat. aqNaHCO3 (3 × 10 mL), sat. aq Na2S2O3 (3 × 10 mL), and brine (3 ×10 mL), then dried (MgSO4). Column chromatography (silica gel,1% EtOAc-hexanes) gave a pale-yellow solid.yield: 0.96 g (83%). |
| 36% |
at 85℃; for 15h; Inert atmosphere; |
|
|
With sulfuric acid |
|
|
With sodium acetate anschliessendes Erhitzen mit Acetanhydrid und Pyridin; |
|
|
With sodium acetate |
|
|
In pyridine Yield given; |
|
|
Heating; |
|
|
With Sm{N<SO2OCH(CF3)2>2}3 In dichloromethane at 30℃; |
|
| 99 % Chromat. |
at 25℃; for 2h; |
|
| 98 % Chromat. |
With K5<CoW12O40> at 20℃; for 0.05h; |
|
| 99 % Chromat. |
With bismuth(lll) trifluoromethanesulfonate at 25℃; for 2.5h; |
|
|
With 4 A molecular sieve In hexane at 80℃; for 24h; |
|
| 96 % Chromat. |
In dimethyl sulfoxide at 20℃; for 5h; |
|
|
at 20℃; for 0.25h; |
|
| 100 %Chromat. |
With [Ti(IV)(salophen)(OTf)2] In dichloromethane at 20℃; for 0.0166667h; |
|
| 97 %Chromat. |
With sulfonated ordered mesoporous carbon (CMK-5-SO3H) In neat (no solvent) at 20℃; for 0.166667h; Green chemistry; |
|
|
at 50 - 60℃; |
1 Esterification reaction:
A dry 500 ml four-necked flask equipped with a thermometer, a stirring paddle, and a reflux condenser was charged with 99.3% of phenylethyl alcohol: 50.0 g (0.407 mol), and acetic anhydride: 210 g (2.038 mol). The outer wall of the four-necked flask was incubated with warm water, and the internal temperature was controlled at 50 to 60 ° C for esterification. During the reaction, the content of the reaction liquid was detected by gas chromatography, and the residual phenylethyl alcohol at the end of the reaction was controlled to be ≤ 0.2%, and the reaction time was generally 5 to 8 hours. |
|
With acyltransferase; water In aq. phosphate buffer at 40℃; for 0.166667h; Enzymatic reaction; |
|
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