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Cas Database

60-12-8

60-12-8

Identification

  • Product Name:Phenethyl alcohol

  • CAS Number: 60-12-8

  • EINECS:200-456-2

  • Molecular Weight:122.167

  • Molecular Formula: C8H10O

  • HS Code:29062990

  • Mol File:60-12-8.mol

Synonyms:Phenethylalcohol (8CI);(2-Hydroxyethyl)benzene;2-Phenethanol;2-Phenethyl alcohol;2-Phenyl-1-ethanol;Benzyl carbinol;Ethanol, 2-phenyl-;NSC 406252;PEA;Phenethanol;b-(Hydroxyethyl)benzene;b-PEA;b-Phenethanol;b-Phenethyl alcohol;b-Phenylethanol;b-Phenylethyl alcohol;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Warning

  • Hazard Statement:H319 Causes serious eye irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Rinse and then wash skin with water and soap. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. Refer for medical attention . Minimum/Potential Fatal Human Dose3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG; BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

  • Fire-fighting measures: Suitable extinguishing media Use water spray, powder, alcohol-resistant foam, carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong oxidants, strong acids and food and feedstuffs. Well closed. Keep in a well-ventilated room.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:Phenyl ethyl alcohol
  • Packaging:100g
  • Price:$ 389
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  • Manufacture/Brand:TRC
  • Product Description:Phenethyl alcohol
  • Packaging:25g
  • Price:$ 95
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Phenylethyl Alcohol >98.0%(GC)
  • Packaging:25mL
  • Price:$ 17
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Phenylethyl Alcohol >98.0%(GC)
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  • Price:$ 37
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenethyl alcohol natural, ≥99%, FCC, FG
  • Packaging:1 kg
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenethyl alcohol natural, ≥99%, FCC, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenethyl alcohol ≥99%, FCC, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenylethyl alcohol United States Pharmacopeia (USP) Reference Standard
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenethyl alcohol ≥99%, FCC, FG
  • Packaging:25 kg
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenethyl alcohol ≥99%, FCC, FG
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Relevant articles and documentsAll total 836 Articles be found

-

Dauben,Coad

, p. 2928 (1949)

-

Nitrogen and sulfur co-doped cobalt carbon catalysts for ethylbenzene oxidation with synergistically enhanced performance

Chen, Sheng,Wu, Yujie,Jie, Shanshan,Au, Chak Tong,Liu, Zhigang

, p. 9462 - 9467 (2019)

Heteroatom doping has been demonstrated to be an effective strategy for improving the performance of catalysts. In this paper, cobalt carbon catalysts co-doped with nitrogen and sulfur (N and S) were synthesized through a hydrothermal method with chelate composites involving melamine, thioglycolic acid (C2H4O2S), and tetrahydrate cobalt acetate (Co(OAc)2·4H2O). In addition, the selective oxidation of ethylbenzene under solvent-free conditions with molecular oxygen was used as a probe reaction to evaluate the activity of the catalysts. The optimized catalyst shows an ethylbenzene conversion of 48% with an acetophenone selectivity of 85%. Furthermore, the catalysts were systematically characterized by techniques such as TEM, SEM, XRD, Raman, and XPS. The results reveal that the species of cobalt sulfides and synergistic effects between N and S has inserted a key influence on their catalytic performance.

Tetrahedral Sn-silsesquioxane: Synthesis, characterization and catalysis

Beletskiy, Evgeny V.,Shen, Zhongliang,Riofski, Mark V.,Hou, Xianliang,Gallagher, James R.,Miller, Jeffrey T.,Wu, Yuyang,Kung, Harold H.,Kung, Mayfair C.

, p. 15699 - 15701 (2014)

A tetrahedral stannasilsesquioxane complex was synthesized as a racemic mixture using Sn(OiPr)4 and silsesquioxanediol, and its structure was confirmed with X-ray crystallography, NMR, and EXAFS. The complex was a Lewis acid, and both anti and syn-binding with Lewis bases were possible with the formation of octahedral Sn complexes. It was also a Lewis acid catalyst active for epoxide ring opening and hydride transfer.

A study of factors affecting α-(N-carbamoyl)alkylcuprate chemistry

Dieter,Topping,Nice

, p. 2302 - 2311 (2001)

The effect of Cu(I) salt (i.e., CuCN, CuCN·2LiCl, CuI), cuprate reagent, sec-butyllithium quality, solvent, and temperature upon the chemical yields obtained in the reactions of α-(N-carbamoyl)alkylcuprates [i.e., N-Boc-protected α-aminoalkylcuprates] with (E)1-iodo-1-hexene, 5,5-dimethyl-2-cyclohexenone, methylvinyl ketone, crotonate esters, and an acid chloride has been examined. Cuprate conjugate addition and vinylation reactions can succeed with low-quality sec-butyllithium, presumably containing insoluble lithium hydride and lithium alkoxide impurities, although yields are significantly lower than those obtained with high-quality s-BuLi, α-(N-Carbamoyl)alkylcuprates prepared from high-quality sec-butyllithium are thermally stable for 2-3 h at room temperature and are equally effective when prepared from either insoluble CuCN or THF-soluble CuCN·2LiCl. Use of the latter reagent permits rapid cuprate formation at -78 °C, thereby avoiding the higher temperatures required for cuprate formation from THF-insoluble CuCN that are problematic with solutions containing thermally unstable α-lithiocarbamates.

Biocatalytic reaction and recycling by using CO2-induced organic-aqueous tunable solvents

Broering, James M.,Hill, Elizabeth M.,Hallett, Jason P.,Liotta, Charles L.,Eckert, Charles A.,Bommarius, Andreas S.

, p. 4670 - 4673 (2006)

(Chemical Equation Presented) Tamed OATS: A scheme that integrates homogeneous biocatalysis in organic-aqueous mixtures with CO2-induced separation has been developed. This method allows for simultaneous product recovery and recycling of the homogeneous biocatalyst for reuse.

Altman,Li

, p. 2493 (1976)

Mono- and binuclear complexes of iron(II) and iron(III) with an N 4O ligand: Synthesis, structures and catalytic properties in alkane oxidation

Li, Fei,Wang, Mei,Ma, Chengbing,Gao, Aiping,Chen, Hongbo,Sun, Licheng

, p. 2427 - 2434 (2006)

Three mononuclear iron complexes and one binuclear iron complex, [Fe(tpoen)Cl]·0.5(Fe2OCl6) (1), [Fe(tpoen)Cl]PF6 (2), Fe(tpoen)Cl3 (3) and [{Fe(tpoen)}2(-O)](ClO4)4 (4) (tpoen = N-(2-pyridylmethoxyethyl)-N,N-bis(2-pyridylmethyl)amine), were synthesized as functional models of non-heme iron oxygenases. Crystallographic studies revealed that the Fe(ii) center of 1 is in a pseudooctahedral environment with a pentadentate N4O ligand and a chloride ion trans to the oxygen atom. The Fe(iii) center of 3 is ligated by three nitrogen atoms of tpoen and three chloride ions in a facial configuration. Each Fe(iii) center of 4 is coordinated with four nitrogen atoms and an oxygen atom of tpoen with the Fe-O-Fe angle of 172.0(3) A. Complexes 2, 3 and 4 catalysed the oxidation of cyclohexane with H2O2 in the total TNs of 24-36 with A/K ratios of 1.9-2.4. Under the same conditions they also catalysed both the oxidation of ethylbenzene to benzylic alcohol and acetobenzene with good activity (30-47 TN) and low selectivity (A/K 0.7), and the oxidation of adamantane with moderate activity (15-18 TN) and low regioselectivity (3°/2° 3.0-3.2). With mCPBA as oxidant the catalytic activities of 2, 3 and 4 increased 1.8 to 2.3-fold for the oxidation of cyclohexane and ethylbenzene and 6.3 to 7.5-fold for the oxidation of adamantane. Drastic enhancement of the regioselectivity was observed in the oxidation of adamantane (3°/2° 18.5-30.3). The Royal Society of Chemistry 2006.

Scale-up biopolymer-chelated fabrication of cobalt nanoparticles encapsulated in N-enriched graphene shells for biofuel upgrade with formic acid

Zhou, Shenghui,Dai, Fanglin,Dang, Chao,Wang, Ming,Liu, Detao,Lu, Fachuang,Qi, Haisong

, p. 4732 - 4747 (2019)

Exploring both high-performance catalytic materials from non-edible lignocellulosic biomass and selective hydrodeoxygenation of bioderived molecules will enable value-added utilization of renewable feedstocks to replace rapidly diminishing fossil resources. Herein, we developed a scale-up and sustainable method to fabricate gram-quantities of highly dispersed cobalt nanocatalysts sheathed in multilayered N-doped graphene (Co@NG) by using a biomacromolecule carboxymethyl cellulose (CMC) as a raw material. The ionic gelation of CMC, urea and Co2+ ions leads to uniform dispersion and chelation of different species, consequently resulting in the formation of highly distributed Co nanoparticles (NPs) (10.91 nm) with N-enriched graphene shells in the solid-state thermolysis process. The usage of urea as a non-corrosive activation agent can introduce a porous belt-like nanostructure and abundant doped nitrogen. Among all the prepared catalysts in this work, the optimized Co@NG-6 with the largest specific surface area (627 m2 g-1), the most and strongest basic sites, and the highest proportion of pyridinic-N (37.6%) and mesopores exhibited excellent catalytic activity (99% yield of 2-methoxy-p-cresol) for base-free transfer hydrodeoxygenation (THD) of vanillin using bioderived formic acid (FA) as a H source at 160 °C for 6 h. The poisoning tests and electron paramagnetic resonance (EPR) spectra verified that the strong interaction between N atoms and encapsulated Co NPs provided synergistic effects, which were essential for the outstanding catalytic performance of Co@NG-6. The deuterium kinetic isotope effect study clearly demonstrated that the formation of Co-H-via β-hydride elimination and protonation was the rate-determining step, and protic N-H+ and hydridic Co-H- were considered to be active intermediate species in the THD reaction. Furthermore, Co@NG-6 was highly stable for recycling owing to the graphene shells preventing Co NPs from corrosion and aggregation.

Soft ruthenium and hard Br?nsted acid combined catalyst for efficient cleavage of allyloxy bonds. Application to protecting group chemistry

Tanaka, Shinji,Suzuki, Yusuke,Saburi, Hajime,Kitamura, Masato

, p. 6559 - 6568 (2015)

Abstract We show that a monocationic CpRu(II) complex of quinaldic acid (QAH) and a monocationic CpRu(IV)(π-allyl)QA complex catalyze efficient cleavage of the allyloxy bond in allyl ethers, allyl esters, allyl carbonates, and allyl carbamates in methanol without the need for additional nucleophiles. The only co-product is volatile allyl methyl ether, enhancing operational simplicity during isolation of the deprotected alcohols, acids, and amines. This clean and high-performance catalytic system should contribute to protecting group chemistry during the multistep synthesis of pharmaceutically important natural products. Full details of this system, including the mechanism, are reported.

Regiodivergent Reductive Opening of Epoxides by Catalytic Hydrogenation Promoted by a (Cyclopentadienone)iron Complex

De Vries, Johannes G.,Gandini, Tommaso,Gennari, Cesare,Jiao, Haijun,Pignataro, Luca,Stadler, Bernhard M.,Tadiello, Laura,Tin, Sergey

, p. 235 - 246 (2022/01/03)

The reductive opening of epoxides represents an attractive method for the synthesis of alcohols, but its potential application is limited by the use of stoichiometric amounts of metal hydride reducing agents (e.g., LiAlH4). For this reason, the corresponding homogeneous catalytic version with H2 is receiving increasing attention. However, investigation of this alternative has just begun, and several issues are still present, such as the use of noble metals/expensive ligands, high catalytic loading, and poor regioselectivity. Herein, we describe the use of a cheap and easy-To-handle (cyclopentadienone)iron complex (1a), previously developed by some of us, as a precatalyst for the reductive opening of epoxides with H2. While aryl epoxides smoothly reacted to afford linear alcohols, aliphatic epoxides turned out to be particularly challenging, requiring the presence of a Lewis acid cocatalyst. Remarkably, we found that it is possible to steer the regioselectivity with a careful choice of Lewis acid. A series of deuterium labeling and computational studies were run to investigate the reaction mechanism, which seems to involve more than a single pathway.

One-Pot Bioelectrocatalytic Conversion of Chemically Inert Hydrocarbons to Imines

Chen, Hui,Tang, Tianhua,Malapit, Christian A.,Lee, Yoo Seok,Prater, Matthew B.,Weliwatte, N. Samali,Minteer, Shelley D.

supporting information, p. 4047 - 4056 (2022/02/10)

Petroleum hydrocarbons are our major energy source and an important feedstock for the chemical industry. With the exception of combustion, the deep conversion of chemically inert hydrocarbons to more valuable chemicals is of considerable interest. However, two challenges hinder this conversion. One is the regioselective activation of inert carbon-hydrogen (C-H) bonds. The other is designing a pathway to realize this complicated conversion. In response to the two challenges, a multistep bioelectrocatalytic system was developed to realize the one-pot deep conversion from heptane to N-heptylhepan-1-imine under mild conditions. First, in this enzymatic cascade, a bioelectrocatalytic C-H bond oxyfunctionalization step based on alkane hydroxylase (alkB) was applied to regioselectively convert heptane to 1-heptanol. By integrating subsequent alcohol oxidation and bioelectrocatalytic reductive amination steps based on an engineered choline oxidase (AcCO6) and a reductive aminase (NfRedAm), the generated 1-heptanol was successfully converted to N-heptylhepan-1-imine. The electrochemical architecture provided sufficient electrons to drive the bioelectrocatalytic C-H bond oxyfunctionalization and reductive amination steps with neutral red (NR) as electron mediator. The highest concentration of N-heptylhepan-1-imine achieved was 0.67 mM with a Faradaic efficiency of 45% for C-H bond oxyfunctionalization and 70% for reductive amination. Hexane, octane, and ethylbenzene were also successfully converted to the corresponding imines. Via regioselective C-H bond oxyfunctionalization, intermediate oxidation, and reductive amination, the bioelectrocatalytic hydrocarbon deep conversion system successfully realized the challenging conversion from inert hydrocarbons to imines that would have been impossible by using organic synthesis methods and provided a new methodology for the comprehensive conversion and utilization of inert hydrocarbons.

Protein powder derived nitrogen-doped carbon supported atomically dispersed iron sites for selective oxidation of ethylbenzene

Cheng, Yujie,Gan, Tao,He, Qian,He, Xiaohui,Huang, Liyun,Ji, Hongbing,Shi, Shaolin,Sun, Qingdi,Wang, Pengbo,Zhang, Hao,Zhang, Xingcong,Zhang, Ying

supporting information, p. 11711 - 11715 (2021/09/06)

Atomically dispersed Fe species embedded in the nitrogen-containing carbon supports (Fe1/NC) are successfully synthesized using a ball milling approach, with commercial protein powder as the nitrogen source. The catalyst exhibits outstanding performance in the oxidation of aromatic compounds containing saturated C-H bonds into corresponding ketones under ambient conditions, which is superior to those of a nanoparticle catalyst (Fen/NC) and a metal-free catalyst (NC).

Process route upstream and downstream products

Process route

styrene oxide
96-09-3

styrene oxide

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

2-phenylethanol
60-12-8

2-phenylethanol

Conditions
Conditions Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen; In toluene; at 75 ℃; for 24h; under 37503.8 Torr; Pressure; Temperature; Reagent/catalyst; regioselective reaction; Catalytic behavior;
99%
With lithium triethylborohydride; In tetrahydrofuran; at 0 ℃; for 0.0833333h; Product distribution;
97%
3%
With Li(1+)*C12H28AlO3(1-); In tetrahydrofuran; hexane; at 0 ℃; for 0.17h; Yields of byproduct given;
95%
With Li(1+)*C12H28AlO3(1-); In tetrahydrofuran; hexane; at 0 ℃; for 0.17h; Yield given. Title compound not separated from byproducts;
95%
With dibutylmagnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; at 40 ℃; for 24h; Solvent; Temperature; regioselective reaction;
95%
With sodium tetrahydroborate; alpha cyclodextrin; In water; for 48h; Title compound not separated from byproducts; Ambient temperature;
17%
66%
With methyltriphenylphosphonium tetrahydroborate; zinc(II) chloride; In dichloromethane; at 20 ℃; for 1h;
63%
21%
With sodium tetrahydroborate; cyclomaltooctaose; In water; for 48h; Title compound not separated from byproducts; Ambient temperature;
53%
24%
With sodium tetrahydroborate; alpha cyclodextrin; In water; for 48h; Product distribution; Ambient temperature; presence of β-, and γ-cyclodextrin; kinetic resolution; further epoxides;
31%
23%
With sodium tetrahydroborate; β‐cyclodextrin; In water; for 48h; Product distribution; Ambient temperature; other epoxides, other cyclodextrins;
66 % Chromat.
17 % Chromat.
With aluminium; nickel dichloride; In tetrahydrofuran; for 0.0833333h; other epoxides;
10 % Chromat.
75 % Chromat.
With sodium tetrahydroborate; In ethanol; at 45 ℃; for 3h; Product distribution; var. solvents, times;
With water; diisobutylaluminium hydride; Product distribution; other organoaluminum reagents; regioselectivity;
With sodium tetrahydroborate; In methanol; tert-butyl alcohol; for 2h; Product distribution; Heating; other solvents, other molar ratio;
With sodium tetrahydroborate; β‐cyclodextrin; In water; for 72h; Ambient temperature;
3 % Chromat.
48 % Chromat.
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium iodide; In 1,2-dimethoxyethane; at 70 ℃; for 1h; Yield given. Yields of byproduct given;
With aluminium; nickel dichloride; In tetrahydrofuran; for 0.0833333h;
75 % Chromat.
10 % Chromat.
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium iodide; In 1,2-dimethoxyethane; for 1.5h; Yield given; Heating;
With methanol; sodium tetrahydroborate; In tert-butyl alcohol; for 1h; Yield given. Yields of byproduct given; Heating;
With sodium tetrahydroborate; In isopropyl alcohol; for 2h; Yield given. Yields of byproduct given; Heating;
With sodium aluminum tetrahydride; In tetrahydrofuran; at 0 ℃; for 6h; Yield given. Yields of byproduct given;
With triethylamine alane; In tetrahydrofuran; for 6h; Ambient temperature;
23 % Chromat.
77 % Chromat.
With lithium aluminium tetrahydride; water; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, 25 deg C, 1 h;
With 1-Methylpyrrolidine; lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1h; Yield given. Yields of byproduct given;
With methanol; lithium borohydride; benzamide; In diethyl ether; for 1.5h; Title compound not separated from byproducts; Heating;
With sodium tetrahydroborate; In methanol; tert-butyl alcohol; for 2h; Yield given. Yields of byproduct given;
With LiPyrrBH3; In tetrahydrofuran; at 0 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With LiPh2InH2; In diethyl ether; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;
With LiH-NICRA; In tetrahydrofuran; for 24h;
92 % Chromat.
5 % Chromat.
With sodium tetrahydroborate; β‐cyclodextrin; In water; at 20 ℃; for 48h;
17 % Spectr.
66 % Spectr.
With LiPyrrBH3; In tetrahydrofuran; benzonitrile; at 25 ℃; for 6h;
With borane N-ethyl-N-isopropylaniline complex; In tetrahydrofuran; for 24h; Title compound not separated from byproducts;
With zinc(II) tetrahydroborate; silica gel; In tetrahydrofuran; for 24h; Yield given. Yields of byproduct given; Ambient temperature;
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; magnesium iodide; In toluene; for 1h; Yield given; Heating;
With sodium tetrahydroborate; In ethanol; for 2h; Yield given. Yields of byproduct given; Heating;
With i-Bu2Al-O-s-Bu; water; diisobutylaluminium hydride; Yield given. Multistep reaction. Yields of byproduct given; 1) heptane, 25 deg C, 20 h;
With (1-azabicyclo{2.2.2}octane)aluminium hydride; In toluene; for 16h; Yield given. Yields of byproduct given; Ambient temperature;
With LiPhInH3; In diethyl ether; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;
With zeolite supported zinc borohydride; In tetrahydrofuran; at 20 ℃; for 12h; Yield given. Yields of byproduct given;
With tert-butyl-N-methyl-N-isopropylamine-borane; In tetrahydrofuran; at 20 ℃; for 24h;
With tricyclohexylphosphineindium trihydride; In toluene; at -78 - 20 ℃; for 15h;
44 % Spectr.
56 % Spectr.
With lithium aluminium tetrahydride; diethyl ether;
With sodium tetrahydroborate; In water; for 6h;
With [1-(2-aminomethylphenyl)-3-methylimidazol-2-ylidene]-(η5-pentamethylcyclopentadienyl)(pyridine)ruthenium(II) hexafluorophosphate; potassium tert-butylate; hydrogen; at 25 ℃; for 3h; under 6000.6 Torr;
ethylbenzene
100-41-4,27536-89-6

ethylbenzene

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

2-phenylethanol
60-12-8

2-phenylethanol

Conditions
Conditions Yield
bei elektrolytischer Oxydation;
With lithium aluminium tetrahydride; Perbenzoic acid; Mechanism; Product distribution; 2.) ether, 30 min, reflux; study of the regioselectivity of autoxidation by reduction of the corresponding oxidation-mixture;
Conditions
Conditions Yield
With sodium tetrahydroborate; 18-crown-6 ether; titanium(III) chloride; In tetrahydrofuran; at 30 ℃; for 3h; Product distribution; various catalyst, temp., and time;
With sodium hydroxide; lithium borohydride; Cp2Ti(BH4); dihydrogen peroxide; multistep reaction: regio- and or stereoselectivities for hydroboration;
With sodium hydroxide; lithium borohydride; dihydrogen peroxide; Cp2Ti(BH4); Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) THF, 65 deg C, 9 h; var. reag. in 1) step: Cp2TiBH4;
With sodium tetrahydroborate; 18-crown-6 ether; dihydrogen peroxide; sodium methylate; bis(cyclopentadienyl)titanium dichloride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, 30 deg C, 3 h, 2.) THF, methanol, 40 deg C;
With sodium hydroxide; lithium borohydride; dihydrogen peroxide; Cp2Ti(BH4); Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) THF, 65 deg C, 9 h (or 19 h), var. reag. in step: Cp2TiBH4 or BH3, or BH3 with LiBH4, add of 18-crown-6, var. temp.;
With sodium tetrahydroborate; 18-crown-6 ether; dihydrogen peroxide; sodium methylate; titanium(III) chloride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, 30 deg C, 3 h, 2.) THF, methanol, 40 deg C;
With sodium hydroxide; lithium borohydride; dihydrogen peroxide; Cp2Ti(BH4); Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) THF, 65 deg C, 9 h; var. reag. in 1) step: Cp2TiBH4 or BH3, or BH3 with LiBH4, NaBH4 and 18-crown-6, var. temp. and time;
With benzo[1,3,2]dioxaborole; Pt(COD)Cl2; tricyclohexylphosphine; In tetrahydrofuran; at 25 ℃; for 3h;
With benzo[1,3,2]dioxaborole; tetrakis(triphenylphosphine)platinum; In tetrahydrofuran; at 25 ℃; for 3h;
With isopropyl alcohol; p-benzoquinone; dichloro bis(acetonitrile) palladium(II); 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); In tert-butyl alcohol; at 85 ℃; Product distribution / selectivity;
5.9 %Chromat.
32 %Chromat.
48 %Chromat.
Conditions
Conditions Yield
With oxonium; oxygen; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; Product distribution; regioselectivity of hydroalumination;
95%
5%
With tetrabutylammonium borohydride; benzyl chloride; In tetrahydrofuran; toluene; at 25 ℃; for 4h;
86%
styrene; With 1-bromo-butane; sodium tetrahydroborate; Aliquat 336; at 20 ℃; for 16h;
With sodium hydroxide; dihydrogen peroxide; at 40 ℃; for 1h;
78%
3%
With sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; cobalt(II) chloride; In tetrahydrofuran; 1) CoCl2 - NaBH4, 0 deg C to room temp., 3 h, then alkene, room temp., 3 h;
18%
68%
With sodium hydroxide; borane Ν,Ν-diethylaniline complex; dihydrogen peroxide; Yield given. Multistep reaction. Title compound not separated from byproducts; 1.) toluene, 3 h room temperature, 1 h 50 deg C; 2.) water/methanol/THF;
20%
With ThBHCl*SMe2; dihydrogen peroxide; In dichloromethane; at 25 ℃; for 6h; Other Boron compounds used.;
99 % Chromat.
10%
With dimesitylboron fluoride; In tetrahydrofuran; at 65 ℃; for 24h; Product distribution; Hydroboration/oxydation of alkenes;
With sodium hydroxide; 1-pyrrolylborane; dihydrogen peroxide; Product distribution; other unsaturated hydrocarbons;
86.4 % Chromat.
13.5 % Chromat.
With sodium hydroxide; lithium borohydride; dihydrogen peroxide; ethyl acetate; In diethyl ether; at 25 ℃;
77 % Chromat.
23 % Chromat.
With 1,1'-bis-(diphenylphosphino)ferrocene; sodium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; dihydrogen peroxide; benzo[1,3,2]dioxaborole; Product distribution; Mechanism; var. reaction partner systems also including chiral ligands; other olefins;
With bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; 18-crown-6 ether; In tetrahydrofuran; at 65 ℃; for 5h; Product distribution; various metal borohydrides, crown ethers, and reaction conditions;
With sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; iodine; 1) THF, 25 deg C, 2 h, 2) H2O; other alkenes;
With chloro-trimethyl-silane; MePhBH2Li; dihydrogen peroxide; sodium carbonate; multistep reaction; hydroboration-oxidation of other alkenes;
With benzo[1,3,2]dioxaborole; RhCl(PPh3)3; In tetrahydrofuran; at 25 ℃; Product distribution; other substituted alkenes and alkylenes; var. Rh-catalyst;
10 % Spectr.
90 % Spectr.
With monoaluminum phosphate; zinc(II) tetrahydroborate; In 1,2-dimethoxyethane; for 1h; Product distribution; Ambient temperature; other reagents: SiO2, Al2O3; further alkenes; product selectivity;;
With sodium hydroxide; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; Product distribution; multistep reaction; 1.) 25 deg C, 1 h;
With tetrahydrofuran; sodium hydroxide; borane N-ethyl-N-isopropylaniline complex; dihydrogen peroxide; Product distribution; solvent effects;
With borane-THF; dihydrogen peroxide; sodium carbonate; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, 0 deg C; 2.) H2O/THF, 50 deg C, 1 h;
With sodium hydroxide; 1-pyrrolylborane; dihydrogen peroxide; 1.) THF, 15 h, room temp.; water, 2.) THF, 40-50 deg C, 1 h;
86.4 % Chromat.
13.5 % Chromat.
With sodium hydroxide; diphenylamine borane; dihydrogen peroxide; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) CH2Cl2, 0 deg C, 1 h; 20 deg C, 1 h;
With lithium borohydride; hydroxide; dihydrogen peroxide; benzo[1,3,2]dioxaborole; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, RT, 1 h;
With bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; 18-crown-6 ether; dihydrogen peroxide; sodium methylate; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, 65 deg C, 3 h, 2.) THF, CH3OH, 0.5 h;
With zinc borohydride; silica gel; In 1,2-dimethoxyethane; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;
With sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; iodine; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) THF, 25 deg C, 2 h, 2) H2O;
With sodium hydroxide; dihydrogen peroxide; benzo[1,3,2]dioxaborole; bis(mesityl)niobium; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) THF, 25 deg C, 24 h;
With zinc borohydride; silica gel; In N,N-dimethyl-formamide; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;
With sodium tetrahydroborate; water; dihydrogen peroxide; sodium acetate; copper(l) chloride; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, 25 deg C, 24 h, 2.) 0 deg C;
With sodium hydroxide; N,N-dimethyl acetamide; dihydrogen peroxide; benzo[1,3,2]dioxaborole; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) CH2Cl2, room temperature, 3 h; other reagent: catecholborane, 2.) CH2Cl2, THF, ethanol, room temperature, 2 h;
With sodium hydroxide; dihydrogen peroxide; benzo[1,3,2]dioxaborole; 1.) RhCl3>3; Yield given. Multistep reaction; 1.) CF3C6F11, 40 deg C, 2.) EtOH, THF, 0 deg C, 0.5 h;
With dimesitylboron fluoride; In tetrahydrofuran; at 65 ℃; for 24h; Yields of byproduct given. Title compound not separated from byproducts;
80 % Chromat.
With sodium hydroxide; borane:1,4-oxathiane; dihydrogen peroxide; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, room temp., 5 min;
With sodium hydroxide; diphenylamine borane; dihydrogen peroxide; Yield given. Yields of byproduct given. Title compound not separated from byproducts; 1.) CH2Cl2, 0 deg C, 1 h; 20 deg C, 1 h;
With 1,1'-bis-(diphenylphosphino)ferrocene; sodium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; dihydrogen peroxide; benzo[1,3,2]dioxaborole; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, 25 deg C, 30 min, 2.) THF, RT, 3 h;
With sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; acetic acid; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, r.t., 12 h;
With sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; dihydrogen peroxide; Yield given. Multistep reaction; 1.) diglyme, 25-35 deg C, 1 h; 2.) diglyme, 25-35 deg C;
With sodium tetrahydroborate; (2,3,7,8,12,13,17,18-octaethylporphyrinato)rhodium(III) chloride; oxygen; In tetrahydrofuran; at 20 - 25 ℃; for 50h; Yield given. Yields of byproduct given;
With sodium hydroxide; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; Yield given. Multistep reaction. Yields of byproduct given; 1) pentane, -25 deg C, 1 h; 2) 50 deg C,;
With dihydrogen peroxide; benzo[1,3,2]dioxaborole; samarium (III) iodide; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, r.t., 18 h;
styrene; With tert-butyl-N-methyl-N-isopropylamine-borane; In tetrahydrofuran; at 19 - 25 ℃; for 2h;
With sodium hydroxide; dihydrogen peroxide; In water; at 50 ℃; for 2h;
styrene; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 4h;
With benzene-1,2-diol; triethylamine; In tetrahydrofuran; at 20 ℃; for 2.5h;
With oxygen; In tetrahydrofuran; at 20 ℃; for 12h;
styrene; With benzo[1,3,2]dioxaborole; [Rh(NBD)(S)-BINAPO]BF4; In tetrahydrofuran; at 25 ℃; for 12h;
With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; ethanol; at 25 ℃; for 10h;
styrene; With dioxane-BH2Cl; In 1,4-dioxane; at 20 ℃;
With sodium hydroxide; dihydrogen peroxide; In methanol; water; at 20 - 40 ℃;
styrene; With rhodium(III) chloride; boron trifluoride-tetrahydrofuran complex; In tetrahydrofuran; at 20 ℃; for 2h;
With sodium hydroxide; dihydrogen peroxide; In water;
styrene; With boron trifluoride-tetrahydrofuran complex; In tetrahydrofuran; at 20 ℃; for 2h;
With sodium hydroxide; dihydrogen peroxide; In water;
styrene; With styrene and bis(4-vinylbenzylcyclopentadienyl)ZrCl2 copolym; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; for 8h;
With tert.-butylhydroperoxide; In tetrahydrofuran; for 4h;
styrene; With rhodium(III) chloride; boron trifluoride-tetrahydrofuran complex; In tetrahydrofuran; at 24 ℃; for 2h;
With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 24 ℃;
styrene; With boron trifluoride-tetrahydrofuran complex; In tetrahydrofuran; at 24 ℃; for 2h;
With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 24 ℃;
With benzo[1,3,2]dioxaborole; 1,3-dibutyl-4,5-dichloro-imidazole-1,3-divinylsiloxane Pt(0); In tetrahydrofuran; at 25 ℃; for 3h;
With benzo[1,3,2]dioxaborole; Pt(COD)Cl2; triphenylphosphine; In tetrahydrofuran; at 25 ℃; for 3h;
styrene; In 1,4-dioxane; at 20 ℃;
With alkaline hydrogen peroxide; In 1,4-dioxane; Further stages. Title compound not separated from byproducts.;
styrene; With benzo[1,3,2]dioxaborole; CuI(N-heterocyclic carbene); In tetrahydrofuran; at 25 ℃; for 4h;
With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; Further stages.;
styrene; (50AA)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50AB)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50AC)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50AD)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50AE)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50AH)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50BB)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50BD)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50BF)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50BG)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50CF)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50CG)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50CH)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50DD)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50EI)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50FI)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50GG)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
styrene; (50GI)Rh(cod)Cl;
With sodium hydroxide; dihydrogen peroxide; Product distribution / selectivity;
With benzo[1,3,2]dioxaborole; for 0.166667h;
styrene; With 1,5-cyclooctadienebis(tetrahydrofuran)rhodium(I) tetrafluoroborate; C27H17N2O2P; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; at -30 ℃; for 24h; Inert atmosphere;
With dihydrogen peroxide; sodium hydroxide; Inert atmosphere;
styrene; In tetrahydrofuran; at 0 - 20 ℃; for 16.5h; Inert atmosphere;
With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; regioselective reaction;
84 %Chromat.
13 %Chromat.
styrene; With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; bis(diphenylphosphino)methane borane; benzo[1,3,2]dioxaborole; In tetrahydrofuran; at 25 ℃; for 22h; Inert atmosphere;
With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; ethanol; at 0 - 25 ℃; for 1h; regioselective reaction; Inert atmosphere;
styrene; With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; bis-diphenylphosphinomethane; benzo[1,3,2]dioxaborole; In tetrahydrofuran; at 25 ℃; for 22h; Inert atmosphere;
With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; ethanol; at 0 - 25 ℃; for 1h; regioselective reaction; Inert atmosphere;
With water; isopropyl alcohol; copper dichloride; bis(benzonitrile)palladium(II) dichloride; 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); at 70 ℃; Product distribution / selectivity; Inert atmosphere;
9.6 %Chromat.
51 %Chromat.
With dichloro bis(acetonitrile) palladium(II); 1-hydroxytetraphenyl-cyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); water; p-benzoquinone; In isopropyl alcohol; at 35 - 85 ℃; for 34h; Inert atmosphere; Glovebox;
57 %Chromat.
10 %Chromat.
styrene; With borane-ammonia complex; In tetrahydrofuran; at 90 ℃;
With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; at 0 - 20 ℃;
styrene; With sodium tetrahydroborate; ethyl iodide; In 1,2-dimethoxyethane; at 25 ℃; for 20h;
With dihydrogen peroxide; sodium hydroxide; In water; at 0 - 25 ℃; for 0.333333h; Solvent; Reagent/catalyst; Overall yield = 86 percent;
74 %Spectr.
12 %Spectr.
Conditions
Conditions Yield
With sodium tetrahydroborate; selenium; iron(II) chloride; In ethanol; at 30 ℃; for 2h; Product distribution; Mechanism; effect of solvent and catalysis on reduction of several epoxides; deuterium labelled study;
51 % Chromat.
32 % Chromat.
17 % Chromat.
With zinc(II) tetrahydroborate; monoaluminum phosphate; In tetrahydrofuran; for 24h; Product distribution; Ambient temperature; influence of catalyst on degree of styrene oxide conversion and reaction selectivity; further catalysts;
styrene oxide
96-09-3

styrene oxide

ethylbenzene
100-41-4,27536-89-6

ethylbenzene

2-phenylethanol
60-12-8

2-phenylethanol

Conditions
Conditions Yield
With sodium tert-pentoxide; sodium hydride; nickel dichloride; In 1,2-dimethoxyethane; at 65 ℃; for 2h;
5%
90%
With aluminum oxide; sodium tetrahydroborate; palladium dichloride; In hexane; water; at 30 ℃; for 1h;
84%
14%
With Amberlite IRA-400; borohydride form; nickel diacetate; In methanol; at 20 ℃; for 1h;
89 % Chromat.
11 % Chromat.
With hydrogen; In 1,4-dioxane; at 90 ℃; for 5h; under 750.075 Torr;
80 %Chromat.
12.3 %Chromat.
With hydrogen; In 1,4-dioxane; at 90 ℃; for 3h; under 760.051 Torr; Reagent/catalyst;
ethylbenzene
100-41-4,27536-89-6

ethylbenzene

4-Ethylphenol
123-07-9

4-Ethylphenol

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

2-phenylethanol
60-12-8

2-phenylethanol

Conditions
Conditions Yield
With rabbit liver microsomal cytochrome P-450; In water; at 25 ℃; for 12h;
0.08%
0.13%
99.8%
β-phenylpropionyl peroxide
3070-40-4

β-phenylpropionyl peroxide

1,4-diphenylbutane
1083-56-3

1,4-diphenylbutane

ethylbenzene
100-41-4,27536-89-6

ethylbenzene

2-phenylethanol
60-12-8

2-phenylethanol

3-phenylpropionic acid 2-phenylethyl ester
28049-10-7

3-phenylpropionic acid 2-phenylethyl ester

C<sub>6</sub>H<sub>4</sub>(CH<sub>2</sub>CH<sub>2</sub>C(O)O)
119-84-6,1341-36-2

C6H4(CH2CH2C(O)O)

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

Conditions
Conditions Yield
With P0 silica; at 55 ℃; Rate constant; Product distribution; coadsorbed O2, photolysis, other temperatures;
48.4%
18.2 % Chromat.
2.04 % Chromat.
0.63 % Chromat.
9.3 % Chromat.
3.92 % Chromat.
2-phenylethyl tosylate
4455-09-8

2-phenylethyl tosylate

2-phenylethanol
60-12-8

2-phenylethanol

1-fluoro-2-phenylethane
458-87-7

1-fluoro-2-phenylethane

Conditions
Conditions Yield
With potassium fluoride; In various solvent(s); at 50 - 55 ℃; for 43h; Yields of byproduct given;
81%
2-phenylethyl mesylate
20020-27-3

2-phenylethyl mesylate

2-phenylethanol
60-12-8

2-phenylethanol

1-fluoro-2-phenylethane
458-87-7

1-fluoro-2-phenylethane

Conditions
Conditions Yield
With potassium fluoride; In various solvent(s); at 50 - 55 ℃; for 168h; Yields of byproduct given;
63%

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