Name: 885-77-8|Di-p-tolylmethanol|98%
Brand: Ambeed
SKU: A239660
Rating: 97 (29 reviews)

1
[ 611-97-2 ]
[ 885-77-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogen In tetrahydrofuran at 60℃; for 45h;
97%	With sodium tetrahydridoborate In isopropanol for 19h; Ambient temperature;
97%	With sodium tetrahydridoborate In methanol; acetonitrile at 20℃; for 2h;

96%	With lithium aluminium hydride In diethyl ether for 48h; Heating;
92%	Stage #1: bis(p-methylphenyl)-methanone With (dppe)2Fe(H)2*(C₇H₈)2; Na-tetrakis(ethoxy)borate In toluene at 100℃; for 2h; visible light irradiation; Inert atmosphere; Stage #2: With lithium hydroxide monohydrate; sodium hydroxide In methanol; toluene at 20℃; for 16h;
92%	With C₃₆H₄₆Cl₄N₄Ru₂; isopropanol; sodium hydroxide at 40 - 80℃; for 2h; Inert atmosphere;
90%	With lithium tert-butylate In isopropanol at 20℃; for 24h; UV-irradiation;
50%	With C₈₄H₁₀₂Cl₂Fe₂N₁₄O₁₃⁽²⁺⁾*2Cl^(1-); isopropanol; potassium hydroxide at 80 - 85℃; for 12h; Inert atmosphere; Schlenk technique;
	With diethyl ether; ethanol; benzene weiteres Reagens: Natrium-Amalgam;
	With sodium isopropanolate; isopropanol Irradiation_.bei Luftausschluss unter der Einwirkung von Sonnenlicht;
	With tris isopropylate aluminium
	With sodium tetrahydridoborate
	With pyridine; sodium iodide Electrolysis;
	With sodium hydroxide; zinc
	With sodium mercury amalgam; ethanol
	With ethanol; aluminum amalgam
	With tris isopropylate aluminium In isopropanol
	With pyridine; lithium aluminium hydride In pyridine
	With sodium hydroxide; zinc
	With sodium tetrahydridoborate In isopropanol
	With tris isopropylate aluminium; isopropanol
	With sodium tetrahydridoborate In ethanol
	With lithium aluminium hydride
	With potassium hydroxide; zinc In ethanol
	With lithium aluminium hydride In diethyl ether Heating;
	With sodium tetrahydridoborate In tetrahydrofuran
	With sodium tetrahydridoborate
	With sodium tetrahydridoborate In methanol
	With sodium hydroxide In lithium hydroxide monohydrate	74 3,3-Bis(p-tolyl)propionic acid EXAMPLE 74 3,3-Bis(p-tolyl)propionic acid A suspension of 1.6 g. (942 mmol) of lithium aluminum hydride and 250 ml. of ether is stirred under reflux while 30 g. (143 mmol) of 4,4'-dimethylbenzophenone was added and for 4 hours thereafter. The mixture is cautiously treated with water and dilute sodium hydroxide and filtered. Evaporation of the filtrate yields 28.1 g. of bis(p-tolyl)methanol, m.p. 69°-70° C.
	With sodium hydroxide	59 3,3-Bis(p-tolyl)propionic acid EXAMPLE 59 3,3-Bis(p-tolyl)propionic acid A suspension of 1.6 g. of lithium aluminum hydride and 250 ml. of ether is stirred at reflux while 30 g. of 4,4'-dimethylbenzophenone is added and for 4 hours thereafter. Unreacted hydride is decomposed by the addition of aqueous sodium hydroxide solution, and the mixture is filtered. The filtrate is extracted with ether, and the extract is dried and evaporated to yield 28.1 g. of 4,4'-dimethylbenzhydrol, m.p. 69°-70° C.
	Stage #1: bis(p-methylphenyl)-methanone With sodium tetrahydridoborate In methanol at 20 - 35℃; for 0.5h; Stage #2: In methanol	2 Example - 2 Preparation of 4,4'- Dimethyl benzhydrol (9) To a solution of 4,4 '-dimethyl benzophenone obtained from experiment 1 (50g, 0.23 mol) in methanol (1500 ml) at ambient temperature was added Sodium borohydride (15g, 0.39 mol) in lots maintaining temperature at 30 - 35°C. After complete addition of sodium borohydride, the reaction mixture was stirred for further 30 min.The reaction mixture was adjusted to PH ~7 and methanol was recovered on a rota- evaporator under reduced pressure to give an oily mass which was diluted with water (500ml) and cooled to 10 - 150C to give a solid. The solid was filtered and washed with water and dried (50g, M.Pt. 70 - 720C.)1H NMR (CDCl3): δ 7.26 - 7.23 (m, 4H), 7.14 - 7.11 (m, 4H), 5.77 (s, IH), 2.3 (s, 6H) Mass Spectrum: [M+ Na], 235
	With sodium tetrahydridoborate In methanol
	With sodium tetrahydridoborate
	With sodium tetrahydridoborate In methanol
	Stage #1: bis(p-methylphenyl)-methanone With C₃₃H₅₈FeN₃PSi₂; phenylsilane In toluene at 20℃; for 4h; Inert atmosphere; Glovebox; Green chemistry; Stage #2: With sodium hydroxide In toluene for 1h; Green chemistry;
	With sodium tetrahydridoborate In methanol
	With C₁₀H₁₄Cl₃Ru^(1-)C₁₉H₁₅Cl₃N₃⁽¹⁺⁾H₂O; potassium hydroxide In isopropanol at 82℃; for 4h;
	With C₆₉H₈₁Cl₃Ir₃N₉; potassium hydroxide In isopropanol at 100℃; for 3h; Inert atmosphere; Schlenk technique;
	With sodium tetrahydridoborate In ethanol for 2h; Reflux;	General procedure: A mixture of corresponding substituted benzophenone (6a-d, 15 mmol) and sodium borohydride (13.5 mmol) in ethanol (25 mL) was refluxed for 2 h. Upon completion of the reaction, 2 mL water was added. The solvent was evaporated under reduced pressure, and the residue was dissolved in dichloromethane (20 mL). The organic layer was washed with water (15 mL) and concentrated under reduced pressure to produce corresponding substituted benzhydrylol 7a-d as white solids. The solid (10 mmol) and thionyl chloride (1 mL) in 25 mL dichloromethane in the presence of piperidine (1 drop) were stirred at room temperature for 4 h. The solvent was evaporated under reduced pressure to deliver corresponding substituted benzhydryl chloride 8a-d. A mixture of the residue (10 mmol) and piperazine (50 mmol) in cyclohexane (25mL) was refluxed for 16 h. After completion, the solvent was removed under reduced pressure. The crude compound was dissolved in dichloromethane (75 mL) and was washed with 1 N sodium hydroxide (50 mL) and water (25 mL). The organic layer was evaporated under reduced pressure to provide corresponding 1-(substituted benzhydryl)piperazine 9a-d, yield 76-94%.
	With sodium tetrahydridoborate In methanol
	With C₃₅H₂₅ClF₁₈N₃Rh*CH₄O In isopropanol at 82℃; for 4h;
	With sodium tetrahydridoborate
	Multi-step reaction with 2 steps 1: [CoCl₂(4'-(4-pyridyl)-2,2':6',2''-terpyridine)]·2H₂O; potassium-t-butoxide / tetrahydrofuran / 4 h / 25 °C / Inert atmosphere; Glovebox 2: mesoporous silica / 25 °C / Inert atmosphere; Glovebox
	Multi-step reaction with 2 steps 1: two-dimensional iron(II) coordination polymer based on a divergent 4'-(4-diphenylamino)phenyl-4,2';6',4''-terpyridine ligand; potassium-t-butoxide / tetrahydrofuran / 16 h / 25 °C / Inert atmosphere; Glovebox 2: mesoporous silica; lithium hydroxide monohydrate / ethyl acetate; hexane / 25 °C / Inert atmosphere; Glovebox
	Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 0 °C / Inert atmosphere 2: sodium hydroxide / tetrahydrofuran; hexane; lithium hydroxide monohydrate / 0.5 h
	With sodium tetrahydridoborate Inert atmosphere;
94 %Spectr.	With C₂₄H₃₁CeF₁₀N₄OSi₂; 1,1,3,3-tetramethyldisiloxane In benzene at 20℃; for 20h; Inert atmosphere; Glovebox;
	Multi-step reaction with 2 steps 1: lithium bromide / 1 h / 24 - 25 °C / Inert atmosphere 2: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran; lithium hydroxide monohydrate / 1 h / 20 °C
	Multi-step reaction with 2 steps 1: 0.55C₂₇H₄₃N₃Si₃V*0.45C₂₇H₄₄N₃Si₃V / diethyl ether / 2 h / 20 °C / Inert atmosphere; Glovebox; Schlenk technique 2: air / diethyl ether
	Multi-step reaction with 2 steps 1: C₃₀H₄₆CoN₄O₂ / toluene / 18 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: N,N,N-tributylbutan-1-aminium fluoride / dichloromethane; tetrahydrofuran / Inert atmosphere; Schlenk technique; Glovebox
81 %Spectr.	With [Ru(CO₃)(N,N′-dimethyl-imidazol-2-ylidene)(p-cymene)]; isopropanol; potassium hydroxide at 80℃; for 0.666667h; Inert atmosphere;
	Multi-step reaction with 2 steps 1: C₂₂H₁₅FeNO₃ / toluene / 12 h / 50 °C / Inert atmosphere; Sealed tube 2: lithium hydroxide monohydrate

Reference： [1]Zhang, Guoqi; Scott, Brian L.; Hanson, Susan K. [Angewandte Chemie - International Edition, 2012, vol. 51, # 48, p. 12102 - 12106][Angew. Chem., 2012, p. 12077]
[2]Pavia, Michael R.; Lobbestael, Sandra J.; Nugiel, David; Mayhugh, Daniel R.; Gregor, Vlad E.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 22, p. 4238 - 4248]
[3]Kodama, Shintaro; Hashidate, Suguru; Nomoto, Akihiro; Yano, Shigenobu; Ueshima, Michio; Ogawa, Akiya [Chemistry Letters, 2011, vol. 40, # 5, p. 495 - 497]
[4]Ohwada, Tomohiko; Shudo, Koichi [Journal of Organic Chemistry, 1989, vol. 54, # 22, p. 5227 - 5237]
[5]Castro, Luis C. Misal; Bezier, David; Sortais, Jean-Baptiste; Darcel, Christophe [Advanced Synthesis and Catalysis, 2011, vol. 353, # 8, p. 1279 - 1284]
[6]Viji, Mambattakkara; Tyagi, Nidhi; Naithani, Neeraj; Ramaiah, Danaboyina [New Journal of Chemistry, 2017, vol. 41, # 21, p. 12736 - 12745]
[7]Cao, Dawei; Xia, Shumei; Pan, Pan; Zeng, Huiying; Li, Chao-Jun; Peng, Yong [Green Chemistry, 2021, vol. 23, # 19, p. 7539 - 7543]
[8]Ramaiah, Danaboyina; Tyagi, Nidhi; Viji, Mambattakkara [New Journal of Chemistry, 2022]
[9]Bachmann [Journal of the American Chemical Society, 1933, vol. 55, p. 770,773]
[10]Bachmann [Journal of the American Chemical Society, 1933, vol. 55, p. 391,394]
[11]Picard; Kearns [Canadian Journal of Research, Section B: Chemical Sciences, 1950, vol. 28, p. 56,58]
[12]McEwen et al. [Journal of the American Chemical Society, 1956, vol. 78, p. 4587]
[13]McEwen et al. [Journal of the American Chemical Society, 1956, vol. 78, p. 4587]
[14]Norris; Blake [Journal of the American Chemical Society, 1928, vol. 50, p. 1811]
[15]Weiler [Chemische Berichte, 1874, vol. 7, p. 1184]
[16]Cohen [Recueil des Travaux Chimiques des Pays-Bas, 1919, vol. 38, p. 121]
[17]Iliceto,A. et al. [Gazzetta Chimica Italiana, 1960, vol. 90, p. 919 - 940]
[18]Lansbury,P.T.; Peterson,J.O. [Journal of the American Chemical Society, 1963, vol. 85, p. 2236 - 2242]
[19]Yung; Gilroy; Mahony [Journal of Pharmaceutical Sciences, 1978, vol. 67, # 7, p. 900 - 905]
[20]Mindl,J.; Vecera,M. [Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 1143 - 1149]
[21]Muraoka,M. et al. [Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 860 - 866]
[22]König; Geiger [Chemische Berichte, 1970, vol. 103, # 7, p. 2041 - 2051]
[23]Lee,D.G.; Raptis,M. [Tetrahedron, 1973, vol. 29, p. 1481 - 1486]
[24]Schneider, Reinhard; Mayr, Herbert; Plesch, Peter H. [Berichte der Bunsen-Gesellschaft, 1987, vol. 91, p. 1369 - 1374]
[25]Wang, Zhao; Chandler, W. David; Lee, Donald G. [Canadian Journal of Chemistry, 1998, vol. 76, # 6, p. 919 - 928]
[26]McCalmont, William F.; Heady, Tiffany N.; Patterson, Jaclyn R.; Lindenmuth, Michael A.; Haverstick, Doris M.; Gray, Lloyd S.; Macdonald, Timothy L. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3691 - 3695]
[27]Thiemann, Thies [Journal of Chemical Research, 2007, # 9, p. 528 - 534]
[28]Denegri, Bernard; Kronja, Olga [Journal of Organic Chemistry, 2007, vol. 72, # 22, p. 8427 - 8433]
[29]Current Patent Assignee: PFIZER INC - US4603145, 1986, A
[30]Current Patent Assignee: PFIZER INC - US4536346, 1985, A
[31]Current Patent Assignee: FRESENIUS SE & CO. KGAA - WO2007/74474, 2007, A1 Location in patent: Page/Page column 14; 15-16
[32]Location in patent: experimental part Thiemann, Thies [Letters in Organic Chemistry, 2009, vol. 6, # 7, p. 515 - 525] Location in patent: experimental part Matic, Mirela; Denegri, Bernard; Kronja, Olga [European Journal of Organic Chemistry, 2010, # 31, p. 6019 - 6024]
[33]Location in patent: scheme or table Hu, Chuan; Sun, Zhi-Gang; Wei, Cheng-Xi; Quan, Zhe-Shan [Letters in drug design and discovery, 2010, vol. 7, # 9, p. 661 - 664]
[34]Location in patent: experimental part Nath, Naba K.; Nilapwar, Sanjay; Nangia, Ashwini [Crystal Growth and Design, 2012, vol. 12, # 3, p. 1613 - 1625]
[35]Ruddy, Adam J.; Kelly, Colin M.; Crawford, Sarah M.; Wheaton, Craig A.; Sydora, Orson L.; Small, Brooke L.; Stradiotto, Mark; Turculet, Laura [Organometallics, 2013, vol. 32, # 19, p. 5581 - 5588]
[36]Juric, Sandra; Kronja, Olga [Journal of Physical Organic Chemistry, 2015, vol. 28, # 5, p. 314 - 319]
[37]Kishan, Ram; Kumar, Robin; Baskaran, Sambath; Sivasankar, Chinnappan; Thirupathi, Natesan [European Journal of Inorganic Chemistry, 2015, vol. 2015, # 19, p. 3182 - 3194]
[38]Maity, Ramananda; Mekic, Amel; Van Der Meer, Margarethe; Verma, Amit; Sarkar, Biprajit [Chemical Communications, 2015, vol. 51, # 82, p. 15106 - 15109]
[39]Zhong, Yan; Xu, Yi; Zhang, Ai-Xia; Li, Xiao-Feng; Xu, Zhao-Ying; Li, Ping; Wu, Bin [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2526 - 2530]
[40]Matić, Mirela; Katić, Matija; Denegri, Bernard; Kronja, Olga [Journal of Organic Chemistry, 2017, vol. 82, # 15, p. 7820 - 7831]
[41]Kumar, Robin; Thirupathi, Natesan [RSC Advances, 2017, vol. 7, # 54, p. 33890 - 33904]
[42]Hemalatha; Asghar, Basim H.; Mansoor, S Sheik [Asian Journal of Chemistry, 2018, vol. 30, # 4, p. 821 - 826]
[43]Wu, Jing; Zeng, Haisu; Cheng, Jessica; Zheng, Shengping; Golen, James A.; Manke, David R.; Zhang, Guoqi [Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9442 - 9448]
[44]Li, Li; Liu; Cheng, Jessica; Zhang, Guoqi [Dalton Transactions, 2018, vol. 47, # 29, p. 9579 - 9584]
[45]Yang, Su Jin; Jaladi, Ashok Kumar; Kim, Jea Ho; Gundeti, Shankaraiah; An, Duk Keun [Bulletin of the Korean Chemical Society, 2019, vol. 40, # 1, p. 34 - 38]
[46]Ebisawa, Kousuke; Izumi, Kana; Ooka, Yuka; Kato, Hiroaki; Kanazawa, Sayori; Komatsu, Sayura; Nishi, Eriko; Shigehisa, Hiroki [Journal of the American Chemical Society, 2020, vol. 142, # 31, p. 13481 - 13490]
[47]Shinohara, Koichi; Tsurugi, Hayato; Anwander, Reiner; Mashima, Kazushi [Chemistry - A European Journal, 2020, vol. 26, # 62, p. 14130 - 14136]
[48]An, Duk Keun; Choi, Hyeon Seong; Hwang, Hyonseok; Kim, Hanbi; Lee, Ji Hye; Shin, Hye Lim; Yi, Jaeeun [Bulletin of the Korean Chemical Society, 2020, vol. 41, # 10, p. 1009 - 1018]
[49]Zhang, Guoqi; Wu, Jing; Zheng, Shengping; Neary, Michelle C.; Mao, Jincheng; Flores, Marco; Trovitch, Ryan J.; Dub, Pavel A. [Journal of the American Chemical Society, 2020, vol. 142, # 38, p. 16507 - 16509]
[50]Hori, Momoko; Ishikawa, Ryuta; Koga, Yuji; Matsubara, Kouki; Mitsuyama, Tomoaki; Shin, Sayaka [Organometallics, 2021, vol. 40, # 9, p. 1379 - 1387]
[51]Cazin, Catherine S. J.; Guillet, Sébastien G.; Liu, Yaxu; Ma, Xinyuan; Nolan, Steven P. [Dalton Transactions, 2021, vol. 50, # 37, p. 13012 - 13019]
[52]Current Patent Assignee: JIAXING UNIVERSITY - CN113943327, 2022, A

2
[ 885-77-8 ]
[ 13389-70-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; calcium chloride In dichloromethane
88%	With hydrogenchloride In dichloromethane; water at 20℃; for 120h;
	With hydrogenchloride; diethyl ether; calcium chloride; Petroleum ether

	With hydrogenchloride; diethyl ether
	With hydrogenchloride; benzene
	With hydrogenchloride In benzene
	With thionyl chloride In benzene for 0.5h;
	With hydrogenchloride In Petroleum ether
	With hydrogenchloride; calcium chloride In dichloromethane at 0℃;
	With thionyl chloride Heating;
	With hydrogenchloride; calcium chloride In benzene
	With thionyl chloride In benzene Heating;
	With hydrogenchloride; calcium chloride In dichloromethane; Petroleum ether; benzene
	With hydrogenchloride In dichloromethane at 0℃;
	With hydrogenchloride In dichloromethane for 1h; cooling;
		74 3,3-Bis(p-tolyl)propionic acid A solution of 28.1 g. (13 mmol) of bis(p-tolyl)methanol in 200 ml. of ether was treated with anhydrous hydrogen chloride and then filtered. Evaporation of the filtrate followed by recrystallization from petroleum ether yields 24.4 g. of bis(p-tolyl)methyl chloride, m.p. 42°-43° C.
	With hydrogenchloride	59 3,3-Bis(p-tolyl)propionic acid An ether solution of the 28.1 g. of 4,4'-dimethylbenzhydrol is treated with anhydrous hydrogen chloride and stirred at about 25° C. Evaporation followed by crystallization from petroleum ether affords 24.4 g. of 4,4'-dimethylbenzhydryl chloride as a white solid.
	With thionyl chloride In dichloromethane
	With piperidine; thionyl chloride In dichloromethane at 20℃; for 4h;	General procedure: A mixture of corresponding substituted benzophenone (6a-d, 15 mmol) and sodium borohydride (13.5 mmol) in ethanol (25 mL) was refluxed for 2 h. Upon completion of the reaction, 2 mL water was added. The solvent was evaporated under reduced pressure, and the residue was dissolved in dichloromethane (20 mL). The organic layer was washed with water (15 mL) and concentrated under reduced pressure to produce corresponding substituted benzhydrylol 7a-d as white solids. The solid (10 mmol) and thionyl chloride (1 mL) in 25 mL dichloromethane in the presence of piperidine (1 drop) were stirred at room temperature for 4 h. The solvent was evaporated under reduced pressure to deliver corresponding substituted benzhydryl chloride 8a-d. A mixture of the residue (10 mmol) and piperazine (50 mmol) in cyclohexane (25mL) was refluxed for 16 h. After completion, the solvent was removed under reduced pressure. The crude compound was dissolved in dichloromethane (75 mL) and was washed with 1 N sodium hydroxide (50 mL) and water (25 mL). The organic layer was evaporated under reduced pressure to provide corresponding 1-(substituted benzhydryl)piperazine 9a-d, yield 76-94%.

Reference： [1]Auricchio, Sergio; Magnani, Caterina; Truscello, Ada M. [European Journal of Organic Chemistry, 2002, # 14, p. 2411 - 2416]
[2]Berg, Regina; Straub, Johannes; Schreiner, Ella; Mader, Steffen; Rominger, Frank; Straub, Bernd F. [Advanced Synthesis and Catalysis, 2012, vol. 354, # 18, p. 3445 - 3450]
[3]Bateman; Hughes; Ingold [Journal of the Chemical Society, 1940, p. 974,978]
[4]Norris; Banta [Journal of the American Chemical Society, 1928, vol. 50, p. 1804] Norris; Blake [Journal of the American Chemical Society, 1928, vol. 50, p. 1811]
[5]Norris; Banta [Journal of the American Chemical Society, 1928, vol. 50, p. 1804] Norris; Blake [Journal of the American Chemical Society, 1928, vol. 50, p. 1811]
[6]Yung; Gilroy; Mahony [Journal of Pharmaceutical Sciences, 1978, vol. 67, # 7, p. 900 - 905]
[7]Bolton, Roger; Burley, Rita E.; Williams, Nigel J. [Australian Journal of Chemistry, 1986, vol. 39, # 4, p. 625 - 634]
[8]Mayr, Herbert; Pock, Rudolf [Chemische Berichte, 1986, vol. 119, # 8, p. 2473 - 2496]
[9]Schneider, Reinhard; Mayr, Herbert; Plesch, Peter H. [Berichte der Bunsen-Gesellschaft, 1987, vol. 91, p. 1369 - 1374]
[10]Newman, Amy Hauck; Kline, Richard H.; Allen, Andrew C.; Izenwasser, Sari; George, Clifford; Katz, Jonathan L. [Journal of Medicinal Chemistry, 1995, vol. 38, # 20, p. 3933 - 3940]
[11]Spange, Stefan; Adolph, Simone; Walther, Ralph; Zimmermann, Yvonne [Journal of Physical Chemistry B, 2003, vol. 107, # 1, p. 298 - 305]
[12]Cai, Xiao-Hua; Xie, Bing [Canadian Journal of Chemistry, 2006, vol. 84, # 9, p. 1106 - 1109] Cai, Xiao-Hua; Xie, Bing; Guo, Hui [Canadian Journal of Chemistry, 2006, vol. 84, # 9, p. 1110 - 1113]
[13]Denegri, Bernard; Streiter, Andre; Juric, Sandra; Ofial, Armin R.; Kronja, Olga; Mayr, Herbert [Chemistry - A European Journal, 2006, vol. 12, # 6, p. 1648 - 1656]
[14]Mayr, Herbert; Schimmel, Holger; Kobayashi, Shinjiro; Kotani, Masashi; Prabakaran; Sipos, Laszlo; Faust, Rudolf [Macromolecules, 2002, vol. 35, # 12, p. 4611 - 4615]
[15]Baidya, Mahiuddin; Kobayashi, Shinjiro; Brotzel, Frank; Schmidhammer, Uli; Riedle, Eberhard; Mayr, Herbert [Angewandte Chemie - International Edition, 2007, vol. 46, # 32, p. 6176 - 6179]
[16]Current Patent Assignee: PFIZER INC - US4603145, 1986, A
[17]Current Patent Assignee: PFIZER INC - US4536346, 1985, A
[18]Streidl, Nicolas; Antipova, Anna; Mayr, Herbert [Journal of Organic Chemistry, 2009, vol. 74, # 19, p. 7328 - 7334]
[19]Zhong, Yan; Xu, Yi; Zhang, Ai-Xia; Li, Xiao-Feng; Xu, Zhao-Ying; Li, Ping; Wu, Bin [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2526 - 2530]

3
[ 885-77-8 ]
[ 5831-43-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride Erhitzen des Produkts fuer sich oder mit Pyridin;
	With hydrogen bromide Erhitzen des Produkts fuer sich oder mit Pyridin;

Reference： [1]Gilman; Flick [Recueil des Travaux Chimiques des Pays-Bas, 1929, vol. 48, p. 462]
[2]Gilman; Flick [Recueil des Travaux Chimiques des Pays-Bas, 1929, vol. 48, p. 462]

4
[ 885-77-8 ]
[ 52897-99-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With Acetyl bromide for 0.25h;
58%	With Acetyl bromide In benzene at 20℃; for 6h; Inert atmosphere;
	With hydrogen bromide; acetic acid Erhitzen auf dem Dampfbad, zuletzt unter Zusatz von Acetylbromid;

	With hydrogen bromide; calcium bromide In diethyl ether
	With hydrogen bromide; sodium sulfate In dichloromethane
	With hydrogen bromide Reflux;
	With Acetyl bromide In benzene for 216h; Reflux;

Reference： [1]Location in patent: experimental part Nolte, Christoph; Ammer, Johannes; Mayr, Herbert [Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3325 - 3335]
[2]Padmanaban, Mohan; Biju, Akkattu T.; Glorius, Frank [Organic Letters, 2011, vol. 13, # 1, p. 98 - 101]
[3]Bachmann [Journal of the American Chemical Society, 1933, vol. 55, p. 2135,2136]
[4]Iliceto,A. et al. [Gazzetta Chimica Italiana, 1960, vol. 90, p. 919 - 940]
[5]Denegri, Bernard; Streiter, Andre; Juric, Sandra; Ofial, Armin R.; Kronja, Olga; Mayr, Herbert [Chemistry - A European Journal, 2006, vol. 12, # 6, p. 1648 - 1656]
[6]Location in patent: scheme or table Hu, Chuan; Sun, Zhi-Gang; Wei, Cheng-Xi; Quan, Zhe-Shan [Letters in drug design and discovery, 2010, vol. 7, # 9, p. 661 - 664]
[7]Ahmadi, Abbas; Khalili, Mohsen; Hajikhani, Ramin; Safari, Narjes; Nahri-Niknafs, Babak [Medicinal Chemistry Research, 2012, vol. 21, # 11, p. 3532 - 3540]

5
[ 885-77-8 ]
[ 37858-01-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With iodine In dichloromethane at 25℃; for 1.5h;
	(i) nPrCaI, THF, (ii) (CO₂Et)2; Multistep reaction;

Reference： [1]Jereb, Marjan; Vrazic, Dejan [Organic and Biomolecular Chemistry, 2013, vol. 11, # 12, p. 1978 - 1999]
[2]Lapkin,I.I. et al. [Journal of general chemistry of the USSR, 1972, vol. 42, p. 1374 - 1377][Zhurnal Obshchei Khimii, 1972, vol. 42, p. 1381 - 1384]

6
[ 885-77-8 ]
[ 611-97-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With diisopropyl-carbodiimide In toluene at 120℃; for 24h; Inert atmosphere; Sealed tube;
97%	With dimanganese decacarbonyl In toluene at 120℃; Sealed tube;
92%	With tert.-butylhydroperoxide; bismuth(III) oxide In lithium hydroxide monohydrate; ethyl acetate for 4h; Reflux; chemoselective reaction;

90%	With indium trifluoromethanesulfonate; chloramine-T In acetonitrile for 3.5h; Reflux; Inert atmosphere;	General Experimental Procedure General procedure: The starting 1-(paratolyl)ethanol (1 mmol), chloramine-T (1 mmol), and In(OTf)3(0.3 mmol) were dissolved in CH3CN (10 mL) in a 100 mLflask equipped with a magnetic stirrer and a reflux condenser.The reaction mixture was heated at reflux for 3 h under anArgon atmosphere and was monitored for completion by TLC.After the reaction mixture was cooled to room temperature,the solvent was removed via rotary evaporation. The residueof the reaction mixture was separated through flash columnchromatography on silica gel. The obtained product was confirmed by spectroscopy.
89%	With tert.-butylhydroperoxide; ammonium cerium (IV) nitrate In lithium hydroxide monohydrate; acetonitrile at 20℃; for 9h;
86%	With pyridinium chlorochromate In dichloromethane for 0.5h; Heating;
85%	With sodium trifluoro-methanesulfinate In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube;
72%	With dihydrogen peroxide In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; for 48h;
67%	With Cl2Ru(κ(P)-(η⁶-2-mesityl-1H-inden-3-yl)dicyclohexylphosphine); sodium tertiary butoxide In toluene at 110℃; for 36h; Inert atmosphere; Schlenk technique;
61%	With magnesium sulphate; vanadium(IV) oxide sulphate pentahydrate; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In lithium hydroxide monohydrate at 90℃; for 96h;	4.6 Oxidation of alcohols under open-air atmosphere General procedure: VOSO4·5H2O (126.5 mg, 0.5 mmol), 4,4′-di-tert-butyl-2,2′-bipyridyl (268.4 mg, 1 mmol), and p-nitrobenzhydrol (229.3 mg, 0.05 mmol) were placed in a 100 mL round-bottomed flask, and then water (50 mL) was added. Next, the mixture was stirred, and then anhydrous MgSO4 (18.06 g, 150 mmol) was slowly added into the mixture (cooling by ice water). After that, substrate (10 mmol) was added into the mixture at room temperature, and the mixture was stirred at 90 °C for the appropriate time under open-air atmosphere. After the reaction, the mixture was extracted with ethyl acetate and dried over anhydrous MgSO4. The extracts were concentrated in vacuo. Purification of the products was carried out by silica gel column chromatography using hexane and diethyl ether as eluent to afford the analytically pure ketones. In Table 7 (entries 3, 7, and 8), crude products were purified by recrystallization with ethyl acetate in refrigerator, afforded analytically pure ketones. The product was identified by comparison with the commercially available sample using 1H NMR spectroscopy.
	With bromine; anhydrous Sodium acetate In lithium hydroxide monohydrate; glacial acetic acid at 35℃;
	With pyridinium bromochromate; anhydrous sodium perchlorate In glacial acetic acid at 49.9℃; other temperatures; ΔG(excit.), ΔH(excit.), ΔS(excit.);
	With bromine In glacial acetic acid ΔE(activ.), ΔS(activ.); further reagent - NBS, mercuric acetate;
	With sodium hydrogen sulphate; sulfuric acid In glacial acetic acid at 55℃; ΔE_a, ΔS(excit.);
	Multi-step reaction with 2 steps 1: acetone / Irradiation_.Sonnenlicht 2: benzoquinone-(1.4); benzene; carbon dioxide / Einwirkung von Sonnenlicht
83 %Spectr.	With oxidovanadium(IV) sulfate; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In lithium hydroxide monohydrate at 90℃; for 8h;
	With triethylamine; pyridinium chlorochromate In dichloromethane at 20℃;
	Multi-step reaction with 2 steps 1: hypophosphorous acid; iodine / glacial acetic acid / 60 °C 2: lithium perchlorate / acetonitrile; lithium hydroxide monohydrate / 5 h / 20 °C / Electrolysis
	With (pyridinium)H₃PMo₁₁VO₄₀; dihydrogen peroxide In acetonitrile at 70℃; for 2h; chemoselective reaction;
	With pyridinium chlorochromate In dichloromethane
100 %Chromat.	With C₄₀H₅₆CuN₂O₈Si₂; dihydrogen peroxide In acetonitrile at 60℃; for 4h; Green chemistry;	2.6 Procedure for oxidation reactions General procedure: A two-necked RB flask equipped with a magnetic bar was charged with 10ml acetonitrile. To this, alcohol (1mmol), oxidant (15mmol) and catalyst (16mg for 3 and 50mg for 5-9) were added sequentially. This catalytic mixture was kept under reflux at 60°C until the completion of reaction. The progress of reaction has been monitored by analysing the aliquots of reaction at regular intervals using GC-MS analysis. A Perkin-Elmer gas chromatograph annexed with mass spectrometer (GC-MS CLAURUS 500) was used to analyse the reaction aliquots under the flow of helium carrier gas. The retention time was assigned to the products by comparing with standard values. They were further supported by mass spectrometry. n-Decane was used asan internal standard
	With perchloric acid; tetrabutylammonium bromochromate In lithium hydroxide monohydrate; glacial acetic acid at 29.84℃;	Kinetic measurements: General procedure: A thermostatic water bath was used to maintain the desired temperature within ± 0.1 °C. The calculated amount of the reactants, i.e., benzhydrol (BH), TBABC, perchloric acid, acetic acid and water taken in a reaction vessel which was kept in a thermostatic water bath. After allowing sufficient time to attain the temperature of the experiment, arequisite amount of solutions were rapidly pipetted out into the spectrophotometric cell. The total volume of the reaction mixture was 5 mL in each case. Progress of the reaction was followed by measuring the decrease in [TBABC] by spectrophotometrically at 362 nm using UV-visible spectrophotometer, Shimadzu UV-1800 model. The reaction was carried under pseudo first-order conditions, i.e., [BH] >> [TBABC] in the presence of perchloric acid in 50 % acetic acid - 50 % water medium.
	With C₃₅H₃₁ClN₂O₂PRu*2CH₂Cl₂; N-Methylmorpholine N-oxide In dichloromethane at 20℃; for 12h; Inert atmosphere; Schlenk technique;	2.11. Procedure for catalytic oxidation of alcohols General procedure: Oxidations of primary alcohols to aldehydes and secondary ones to ketones were catalyzed by complexes 1-8 in the presence of N-methylmorpholine-N-oxide (NMO) as co-oxidant. A typical reaction using complexes 1-8 as catalysts is as follows. A solution of each of complexes 1-8 (0.01 mmol) in 10 mL of CH2Cl2 was added to the mixture of substrate (1 mmol) and NMO (2 mmol). The mixture was stirred at room temperature for 12 h and the solvent was evaporated under reduced pressure with a rotary evaporator resulting in a solid mass. Then it was shaken with petroleum ether (30 ~ 40 °C) (20 mL). The oxidized product extracted into petroleum ether was analyzed by GC.
> 99 %Spectr.	With C₃₄H₅₁CeN₅O₈^(1-)C₆H₁₅NH⁽¹⁺⁾; oxygen In N,N-dimethyl-formamide at 120℃; for 20h; Molecular sieve;
	With mesoporous silica; pyridinium chlorochromate In dichloromethane at 20℃;	Synthesis of S3 General procedure: To a solution of S2 (6 mmol) in DCM (20 mL), was added silica gel (about 10 g) and PCC (9.0 mmol, 1.5 equiv). Then the mixture was stirred for overnight at room temperature. The mixture was purified by chromatography eluted with DCM to give S3.
	With dihydrogen peroxide In 1,4-dioxane at 100℃; for 16h; Sealed tube;

Reference： [1]Sueki, Shunsuke; Matsuyama, Mizuki; Watanabe, Azumi; Kanemaki, Arata; Katakawa, Kazuaki; Anada, Masahiro [European Journal of Organic Chemistry, 2020, vol. 2020, # 31, p. 4878 - 4885]
[2]Meng, Shan-Shui; Lin, Li-Rong; Luo, Xiang; Lv, Hao-Jun; Zhao, Jun-Ling; Chan, Albert S. C. [Green Chemistry, 2019, vol. 21, # 22, p. 6187 - 6193]
[3]Location in patent: experimental part Malik, Payal; Chakraborty, Debashis [Synthesis, 2010, # 21, p. 3736 - 3740]
[4]Nakahara, Kazuhide; Kitazawa, Chie; Mineno, Tomoko [Chemical and Pharmaceutical Bulletin, 2017, vol. 65, # 8, p. 801 - 804]
[5]Location in patent: experimental part Gowda, Ravikumar R.; Chakraborty, Debashis [Chinese Journal of Chemistry, 2011, vol. 29, # 11, p. 2379 - 2384]
[6]Dhar; Borden; Tyagarajan; Smith; Branchek; Weinshank; Gluchowski [Journal of Medicinal Chemistry, 1994, vol. 37, # 15, p. 2334 - 2342]
[7]Zhu, Xianjin; Liu, Can; Liu, Yong; Yang, Haijun; Fu, Hua [Chemical Communications, 2020, vol. 56, # 82, p. 12443 - 12446]
[8]Cao, Kuanhong; Deng, Xin; Chen, Tian; Zhang, Qitao; Yu, Lei [Journal of Materials Chemistry A, 2019, vol. 7, # 18, p. 10918 - 10923]
[9]Yuan, Jia; Sun, Yue; Yu, Guang-Ao; Zhao, Cui; She, Neng-Fang; Mao, Shu-Lan; Huang, Peng-Shou; Han, Zhi-Jun; Yin, Jun; Liu, Sheng-Hua [Dalton Transactions, 2012, vol. 41, # 34, p. 10309 - 10316]
[10]Marui, Kuniaki; Higashiura, Yuuki; Kodama, Shintaro; Hashidate, Suguru; Nomoto, Akihiro; Yano, Shigenobu; Ueshima, Michio; Ogawa, Akiya [Tetrahedron, 2014, vol. 70, # 14, p. 2431 - 2438]
[11]Ameta, R.C.; Suresh, K.S.; Shanker, R. [Zeitschrift fur Physikalische Chemie (Leipzig), 1987, vol. 268, # 3, p. 502 - 506]
[12]Narayanan, N.; Balasubramanian, T. R. [Journal of Chemical Research, Miniprint, 1991, # 12, p. 3052 - 3062]
[13]Ameta, R. C.; Suresh, K. S.; Shanker, R. [Zeitschrift fur Physikalische Chemie (Leipzig), 1986, vol. 267, # 6, p. 1227 - 1229]
[14]Saxena, B. B.; Babel, D. K.; Shanker, R. [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1982, vol. 21, # 2, p. 171 - 173]
[15]Schoenberg; Mustafa [Journal of the Chemical Society, 1944, p. 67,70][Journal of the Chemical Society, 1945, p. 657,660]
[16]Kodama, Shintaro; Hashidate, Suguru; Nomoto, Akihiro; Yano, Shigenobu; Ueshima, Michio; Ogawa, Akiya [Chemistry Letters, 2011, vol. 40, # 5, p. 495 - 497]
[17]Li, Hu; Zhu, Ru-Yi; Shi, Wen-Juan; He, Ke-Han; Shi, Zhang-Jie [Organic Letters, 2012, vol. 14, # 18, p. 4850 - 4853,4]
[18]Meng, Li; Su, Jihu; Zha, Zhenggen; Zhang, Li; Zhang, Zhenlei; Wang, Zhiyong [Chemistry - A European Journal, 2013, vol. 19, # 18, p. 5542 - 5545]
[19]Palermo, Valeria; Villabrille, Paula I.; Vazquez, Patricia G.; Caceres, Carmen V; Tundo, Pietro; Romanelli, Gustavo P. [Journal of Chemical Sciences, 2013, vol. 125, # 6, p. 1375 - 1383]
[20]Zheng, Lewei; Huang, Hongli; Yang, Chao; Xia, Wujiong [Organic Letters, 2015, vol. 17, # 4, p. 1034 - 1037]
[21]Antony, Rajendran; Marimuthu, Rajendiran; Vishnoi, Pratap; Murugavel, Ramaswamy [Inorganica Chimica Acta, 2018, vol. 469, p. 173 - 182]
[22]Hemalatha; Asghar, Basim H.; Mansoor, S Sheik [Asian Journal of Chemistry, 2018, vol. 30, # 4, p. 821 - 826]
[23]Tang, Li-Hua; Wu, Fule; Lin, Hui; Jia, Ai-Quan; Zhang, Qian-Feng [Inorganica Chimica Acta, 2018, vol. 477, p. 212 - 218]
[24]Shirase, Satoru; Shinohara, Koichi; Tsurugi, Hayato; Mashima, Kazushi [ACS Catalysis, 2018, vol. 8, # 8, p. 6939 - 6947]
[25]Wang, Chunhai; Huang, Xiaoling; Liu, Xueting; Gao, Suqian; Zhao, Bin; Yang, Shangdong [Chinese Chemical Letters, 2020, vol. 31, # 3, p. 677 - 680]
[26]Zeng, Yan; Chen, Tian; Zhang, Xu; Chen, Ying; Zhou, Hongwei; Yu, Lei [Applied Organometallic Chemistry, 2022, vol. 36, # 6]

7
[ 885-77-8 ]
[ 4957-14-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With iodine; hypophosphorous acid In glacial acetic acid at 60℃; for 24h;
100%	With 1,2-benzenedisulfonimide; isopropanol at 80℃; for 5h;
90%	With iodine; hypophosphorous acid; glacial acetic acid at 40℃; for 5.5h; Inert atmosphere;	3 Example 3:The preparation method of 4,4-dimethyldiphenylmethane of the present embodiment comprises the following steps: (1), 4,4-dimethyldiphenylmethanol (10g),Iodine (11.96g) and acetic acid (300mL)Stir well under nitrogen protection in a flask equipped with a condenser,to obtain the first mixed solution,is the black solution;Among them, the temperature of stirring is 25 ,The stirring time was 3 min.Then add to the first mixtureHypophosphorous acid (50% aq., 23.9 mL),The color of the solution gradually became lighter,to obtain the second mixture,That is, the final yellow-brown solution.(2), after dripping and heating the second mixed solution to 40°C,The heating time is 1.5h,Then stir for 4h,At this time, the solution was pale yellow and clear.TLC detection reaction was completed.Add 300mL of water to dilute,At this point the solution became cloudy,For the white suspension.Extract with PE (300mL),The aqueous phase was washed with 50 mL of PE,The combined organic phases were washed with saturated brine,It was dried over anhydrous Na2SO4 at room temperature and 25°C for 22 h and concentrated to obtain about 9.1 gYellow oily compound.The purity is more than 98%,The yield was 90%.

89%	With palladium (II) chloride In methanol at 40℃; for 18h; Inert atmosphere; Green chemistry; chemoselective reaction;
60%	With benzoyl chloride In 1,3,5-trimethyl-benzene Heating;
	With lithium aluminium hydride; aluminium chloride anhydrous In diethyl ether for 0.25h; Yield given;
	With hydrogen for 20h; Ambient temperature;
	With iodine; hypophosphorous acid In glacial acetic acid at 60℃;
	With palladium (II) chloride In methanol at 40℃; for 24h; Inert atmosphere; Green chemistry;

Reference： [1]Gordon, Paul E.; Fry, Albert J. [Tetrahedron Letters, 2001, vol. 42, # 5, p. 831 - 833]
[2]Location in patent: experimental part Barbero, Margherita; Bazzi, Stefano; Cadamuro, Silvano; Dughera, Stefano; Ghigo, Giovanni [European Journal of Organic Chemistry, 2009, # 25, p. 4346 - 4351]
[3]Current Patent Assignee: SHANGHAI TITAN TECH CO LTD - CN114292154, 2022, A Location in patent: Paragraph 0071-0078
[4]Wang, Hu; Li, Li; Bai, Xing-Feng; Shang, Jun-Yan; Yang, Ke-Fang; Xu, Li-Wen [Advanced Synthesis and Catalysis, 2013, vol. 355, # 2-3, p. 341 - 347]
[5]Luh, Tien-Yau [Synthetic Communications, 1981, vol. 11, # 10, p. 829 - 834]
[6]Popielarz; Arnold [Journal of the American Chemical Society, 1990, vol. 112, # 8, p. 3068 - 3082]
[7]Shapiro, Israel O.; Nir, Malka; Hoffman, Roy E.; Rabinovitz, Mordecai [Journal of the Chemical Society. Perkin transactions II, 1994, # 7, p. 1519 - 1524]
[8]Meng, Li; Su, Jihu; Zha, Zhenggen; Zhang, Li; Zhang, Zhenlei; Wang, Zhiyong [Chemistry - A European Journal, 2013, vol. 19, # 18, p. 5542 - 5545]
[9]Wang, Hu; Li, Li; Bai, Xing-Feng; Deng, Wen-Hui; Zheng, Zhan-Jiang; Yang, Ke-Fang; Xu, Li-Wen [Green Chemistry, 2013, vol. 15, # 9, p. 2349 - 2355]

8
[ 106-38-7 ]
[ 104-87-0 ]
[ 885-77-8 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium 1.) diethyl ether, 2.) 0.5 h; Yield given. Multistep reaction;
	Stage #1: para-bromotoluene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Inert atmosphere; Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran; hexane for 0.333333h; Inert atmosphere; Stage #3: With water In tetrahydrofuran; hexane Inert atmosphere;
	Stage #1: para-bromotoluene; 4-methyl-benzaldehyde With magnesium In tetrahydrofuran at 20 - 85℃; for 2h; Stage #2: In tetrahydrofuran at 0 - 20℃; Inert atmosphere;

Stage #1: para-bromotoluene With magnesium In diethyl ether at 20℃; for 2h; Inert atmosphere; Stage #2: 4-methyl-benzaldehyde In diethyl ether at 20℃; for 2h; Inert atmosphere;

Synthesis of S1 General procedure: To a solution of magnesium(12 mmol, 1.2 equiv) in Et 2 O (10 mL) was added bromobenzene (10.0 mmol, 1.0 equiv) in Et2O (20 mL) very carefully at room temperature under argon atmosphere. The reaction was stirred for about 2h until magnesium was almost disappeared. The resulting Grignard reagent could be used for the next step without further purification.

Reference： [1]Popielarz; Arnold [Journal of the American Chemical Society, 1990, vol. 112, # 8, p. 3068 - 3082]
[2]Zhang, Jiange; Zhang, Pei; Liu, Xianbo; Fang, Kai; Lin, Guoqiang [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3769 - 3773]
[3]Padmanaban, Mohan; Biju, Akkattu T.; Glorius, Frank [Organic Letters, 2011, vol. 13, # 1, p. 98 - 101]
[4]Li, Hu; Zhu, Ru-Yi; Shi, Wen-Juan; He, Ke-Han; Shi, Zhang-Jie [Organic Letters, 2012, vol. 14, # 18, p. 4850 - 4853,4]
[5]Wang, Chunhai; Huang, Xiaoling; Liu, Xueting; Gao, Suqian; Zhao, Bin; Yang, Shangdong [Chinese Chemical Letters, 2020, vol. 31, # 3, p. 677 - 680]

9
[ 104-87-0 ]
[ 4294-57-9 ]
[ 885-77-8 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran for 2h; Heating; Yield given;
	In diethyl ether for 144h; Reflux;
	In diethyl ether

	In tetrahydrofuran at 0 - 20℃;
	In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Dhar; Borden; Tyagarajan; Smith; Branchek; Weinshank; Gluchowski [Journal of Medicinal Chemistry, 1994, vol. 37, # 15, p. 2334 - 2342]
[2]Ahmadi, Abbas; Khalili, Mohsen; Hajikhani, Ramin; Safari, Narjes; Nahri-Niknafs, Babak [Medicinal Chemistry Research, 2012, vol. 21, # 11, p. 3532 - 3540]
[3]Meng, Li; Su, Jihu; Zha, Zhenggen; Zhang, Li; Zhang, Zhenlei; Wang, Zhiyong [Chemistry - A European Journal, 2013, vol. 19, # 18, p. 5542 - 5545]
[4]Zheng, Lewei; Huang, Hongli; Yang, Chao; Xia, Wujiong [Organic Letters, 2015, vol. 17, # 4, p. 1034 - 1037]
[5]Hu, Chen; Hong, Gang; Qian, Xiaofei; Kim, Kwang Rim; Zhu, Xiaoyan; Wang, Limin [Organic and Biomolecular Chemistry, 2017, vol. 15, # 23, p. 4984 - 4991]

10
[ 885-77-8 ]
[ 149110-83-8 ]
O-603 [ No CAS ]
(S)-(+)-2β-carbomethoxy-3α<bis(4-methylphenyl)methoxy>tropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With toluene-4-sulfonic acid In benzene for 23h; Heating;

Reference： [1]Meltzer, Peter C.; Liang, Anna Y.; Madras, Bertha K. [Journal of Medicinal Chemistry, 1996, vol. 39, # 2, p. 371 - 379]

11
[ 885-77-8 ]
[ 622-46-8 ]
[ 64-19-7 ]
[ 285129-99-9 ]
Phenyl N-(4,4'-dimethylbenzhydryl)carbamate [ No CAS ]

Reference： [1]Synthesis,2000,p. 667 - 672

12
[ 885-77-8 ]
bis(4-methylphenyl)methyl nitrite [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With nitrosylchloride; triethylamine In dichloromethane at -78 - -30℃; for 0.5h;

Reference： [1]Tishkov, Alexander A.; Schmidhammer, Uli; Roth, Stefan; Riedle, Eberhard; Mayr, Herbert [Angewandte Chemie - International Edition, 2005, vol. 44, # 29, p. 4623 - 4626]

13
[ 885-77-8 ]
[ 99-33-2 ]
4,4'-dimethylbenzhydryl 3,5-dinitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With pyridine In benzene at 20℃; for 15h;
	With pyridine In benzene

Reference： [1]Denegri, Bernard; Streiter, Andre; Juric, Sandra; Ofial, Armin R.; Kronja, Olga; Mayr, Herbert [Chemistry - A European Journal, 2006, vol. 12, # 6, p. 1648 - 1656]
[2]Location in patent: experimental part Denegri, Bernard; Kronjaa, Olga [Journal of Physical Organic Chemistry, 2009, vol. 22, # 5, p. 495 - 503]

14
[ 201230-82-2 ]
[ 108-88-3 ]
[ 611-97-2 ]
[ 885-77-8 ]
[ 104-87-0 ]
[ 529-20-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 91% 2: 5%	With hydrogen fluoride; boron trifluoride at 45℃; for 1h; Further byproducts.;

Reference： [1]Willemse, J. Alexander; Bezuidenhoudt, Barend C. B.; Holzapfel, Cedric W. [Synthesis, 2006, # 15, p. 2543 - 2550]

15
[ 885-77-8 ]
[ 1885-14-9 ]
[ 957188-24-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With pyridine In benzene at 20℃; for 12h;
	With pyridine In benzene

Reference： [1]Denegri, Bernard; Kronja, Olga [Journal of Organic Chemistry, 2007, vol. 72, # 22, p. 8427 - 8433]
[2]Location in patent: experimental part Denegri, Bernard; Kronjaa, Olga [Journal of Physical Organic Chemistry, 2009, vol. 22, # 5, p. 495 - 503]

16
[ 885-77-8 ]
[ 40673-57-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With Dimethyl oxalate; manganese; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; lithium bromide In N,N-dimethyl-formamide at 110℃; for 16h; Inert atmosphere; Sealed tube;	Synthesis of 2a; Typical Procedure General procedure: The procedure was conducted in an argon-filled glove box. A reaction tube equipped with a magnetic stir bar was charged with Ni(dppe)Cl2(10.6 mg, 0.02 mmol), Mn (44.0 mg, 0.8 mmol), alcohol 1a (48.8 mg,0.4 mmol), DMO (94.5 mg, 0.8 mmol), LiBr (34.7 mg, 0.4 mmol), and DMF (1.5 mL). The reaction tube was then sealed and removed from the glove box. The reaction mixture was stirred at 110 °C for 16 h. After cooling to r.t., the mixture was diluted with EtOAc (40 mL) and washed with water, brine, dried over anhydrous Na2SO4, and concentrated in vacuum. The residue was purified by flash chromatography on silica gel to afford the desired product 2a.
	Multi-step reaction with 2 steps 1: AlCl₃, LiAlH₄ / diethyl ether / 0.25 h 2: 1.) K, NH₃ liq., FeCl₃ / 1.) diethyl ether, 15 min, 2.) overnight
	Multi-step reaction with 2 steps 1: AlCl₃, LiAlH₄ / diethyl ether / 0.25 h 2: 1.) K, NH₃ liq., FeCl₃, 2.) 2-bromo-2-phenylpropane / 1.) diethyl ether, 15 min

Reference： [1]Pan, Feng-Feng; Guo, Peng; Huang, Xiaochuang; Shu, Xing-Zhong [Synthesis, 2021, vol. 53, # 17, p. 3094 - 3100]
[2]Popielarz; Arnold [Journal of the American Chemical Society, 1990, vol. 112, # 8, p. 3068 - 3082]
[3]Popielarz; Arnold [Journal of the American Chemical Society, 1990, vol. 112, # 8, p. 3068 - 3082]

17
[ 885-77-8 ]
[ 55095-22-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diethyl ether; petroleum ether; CaCl₂; HCl 2: aqueous acetone; sodium azide / Hydrierung der mit Pentan extrahierten Anteile des Reaktionsprodukts an Platin in Methanol

Reference： [1]Bateman; Hughes; Ingold [Journal of the Chemical Society, 1940, p. 974,978]

18
[ 885-77-8 ]
[ 562840-43-1 ]
[ 562839-21-8 ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 4h;	117 Example 117; 3-[Bis(4-methylphenyl)methyl)-1-(2-methoxybenzyl)-4-piperidinone To a solution of 2.18 g of 1-(2-methoxybenzyl)-4-piperidinone in 20 ml of dichloromethane were added 4 ml of TMSOTf and then 2.12 g of 4,4'-dimethylbenzhydrol under ice-cooling.. After stirring at room temperature for 4 hours, 20 ml of water was added thereto and the mixture was neutralized with sodium bicarbonate.. The dichloromethane layer was separated, and the solvent was distilled off under reduced pressure.. The residue was purified by silica gel column chromatography (40 g, ethyl acetate: hexane = 1: 4) to obtain 1.4 g of the title compound as an oil.1H-NMR (CDCl3) δ: 2.24 (s, 6H), 2.25-2.95 (m, 6H), 3.32 (m, 1H), 3.56 (s, 2H), 3.77 (s, 3H), 4.56 (d, 1H, J=11.4 Hz), 6.83-7.33 (m, 11H).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1460062, 2004, A1 Location in patent: Page 55

19
4-[4-[2-(2-hydroxyethylthio]ethoxy]phenyl]-1,1,1-trifluoro-2-butanone [ No CAS ]
[ 885-77-8 ]
4-[4-[2-[2-[Bis(4-methylphenyl)methoxy]ethylthio]ethoxy]phenyl]-1,1,1-trifluoro-2-butanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.81 g (94%)	With toluene-4-sulfonic acid In hexane; ethyl acetate; toluene	160 4-[4-[2-[2-[Bis(4-methylphenyl)methoxy]ethylthio]ethoxy]phenyl]-1,1,1-trifluoro-2-butanone Example 160 4-[4-[2-[2-[Bis(4-methylphenyl)methoxy]ethylthio]ethoxy]phenyl]-1,1,1-trifluoro-2-butanone A solution of 4-[4-[2-(2-hydroxyethylthio)ethoxy]phenyl]-1,1,1-trifluoro-2-butanone (1.20 g, 3.72 mmol), 4,4'-dimethylbenzhydrol (0.95 g, 4.47 mmol) and p-toluenesulfonic acid (0.035 g) in toluene (20 ml) was heated under reflux for 15 min. The cooled reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried (magnesium sulfate). Evaporation of the solvent in vacuo and chromatography of the residue on silica gel (elution with a gradient of ethyl acetate 20-40% in hexane) gave 1.81 g (94%) of the title material as an oil. Anal. Calcd. for C29H31F3O3S: C 67.42, H 6.05. Found: C 67.43, H 6.08.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US6255496, 2001, B1 Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US6350892, 2002, B1

20
N-isopropylindole-2-sulfonamide [ No CAS ]
[ 885-77-8 ]
[ 187459-64-9 ]

Yield	Reaction Conditions	Operation in experiment
75%		267 N-Isopropyl-3-[bis(4-methylphenyl)methyl]indole-2-sulfonamide (Compound 266) EXAMPLE 267 N-Isopropyl-3-[bis(4-methylphenyl)methyl]indole-2-sulfonamide (Compound 266) Substantially the same procedure as in Example 266 was repeated using 4,4'-dimethylbenzhydrol (0.96 g, 4.50 mmol) and N-isopropylindole-2-sulfonamide (1.00 g, 4.46 mmol) to give 1.44 g (yield: 75%) of the title compound. 1 H-NMR(CDCl3) δ(ppm): 0.54 (6H, d, J=6.3 Hz), 2.22 (6H, s), 3.0-3.15 (1H, m), 3.69 (1H, d, J=6.9 Hz), 6.22 (1H, s), 6.8-6.9 (2H, m), 6.99 (4H, d, J=8.3 Hz), 7.02 (4H, d, J=8.3 Hz), 7.1-7.2 (1H, m), 7.29 (1H, d, J=8.3 Hz), 8.73 (1H, s).
75%		26 N-Isopropyl-3-[bis(4-methylphenyl)methyl]indole-2-sulfonamide (Compound 26) Example 26 N-Isopropyl-3-[bis(4-methylphenyl)methyl]indole-2-sulfonamide (Compound 26) Substantially the same procedure as in Example 25 was repeated using 4,4'-dimethylbenzhydrol (0.96 g, 4.50 mmol) and N-isopropylindole-2-sulfonamide (1.00 g, 4.46 mmol) to give 1.44 g (yield: 75%) of the title compound. 1H-NMR(CDCl3) δ(ppm): 0.54 (6H, d, J=6.3Hz), 2.22 (6H, s), 3.0-3.15 (1H, m), 3.69 (1H, d, J=6.9Hz), 6.22 (1H, s), 6.8-6.9 (2H, m), 6.99 (4H, d, J=8.3Hz), 7.02 (4H, d, J=8.3Hz), 7.1-7.2 (1H, m), 7.29 (1H, d, J=8.3Hz), 8.73 (1H, s).

Reference： [1]Current Patent Assignee: KIRIN HOLDINGS CO., LTD.; Kyowa Kirin (in: Kirin Holdings) - US5891902, 1999, A
[2]Current Patent Assignee: Kyowa Kirin (in: Kirin Holdings); KIRIN HOLDINGS CO., LTD. - EP782987, 1997, A1

21
[ 3770-50-1 ]
[ 885-77-8 ]
[ 187535-49-5 ]

Yield	Reaction Conditions	Operation in experiment
97%		R.9 Ethyl 3-[bis(4-methylphenyl)methyl]indole-2-carboxylate REFERENCE EXAMPLE 9 Ethyl 3-[bis(4-methylphenyl)methyl]indole-2-carboxylate Substantially the same procedure as in Reference Example 4 was repeated using 4,4'-dimethylbenzhydrol (11.8 g, 55.5 mmol) and ethyl indole-2-carboxylate (10.0 g, 52.9 mmol) to give 19.8 g (yield: 97%) of the title compound. 1 H-NMR(CDCl3) δ(ppm): 1.39 (3H, t, J=7.1 Hz), 2.31 (6H, s), 4.38 (2H, q, J=7.1 Hz), 6.60 (1H, s), 6.85-6.95 (1H, m), 7.0-7.15 (9H, m), 7.2-7.3 (1H, m), 7.35 (1H, d, J=8.6 Hz), 8.82 (1H, s).
97%		R.6 Ethyl 3-[bis(4-methylphenyl)methyl]indole-2-carboxylate Reference Example 6 Ethyl 3-[bis(4-methylphenyl)methyl]indole-2-carboxylate Substantially the same procedure as in Reference Example 1 was repeated using 4,4'-dimethylbenzhydrol (11.8 g, 55.5 mmol) and ethyl indole-2-carboxylate (10.0 g, 52.9 mmol) to give 19.8 g (yield: 97%) of the title compound. 1H-NMR(CDCl3) δ(ppm): 1.39 (3H, t, J=7.1Hz), 2.31 (6H, s), 4.38 (2H, q, J=7.1Hz), 6.60 (1H, s), 6.85-6.95 (1H, m), 7.0-7.15 (9H, m), 7.2-7.3 (1H, m), 7.35 (1H, d, J=8.6Hz), 8.82 (1H, s).

Reference： [1]Current Patent Assignee: KIRIN HOLDINGS CO., LTD.; Kyowa Kirin (in: Kirin Holdings) - US5891902, 1999, A
[2]Current Patent Assignee: KIRIN HOLDINGS CO., LTD.; Kyowa Kirin (in: Kirin Holdings) - EP782989, 1997, A1

22
[ 885-77-8 ]
N-(4,4'-dimethylbenzhydroloxycarbonyl)-ethylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethylenediamine In dichloromethane; water	2 Synthesis of N-(4,4'-dimethylbenzhydroloxycarbonyl)-ethylenediamine (II) Example 2 Synthesis of N-(4,4'-dimethylbenzhydroloxycarbonyl)-ethylenediamine (II) To 130 millimole (mmole) of carbonyldiimidazole (CDI) suspended in 100 mL of dichloromethane (DCM) and stirring at 0° C. was added dropwise a solution of 125 mmole of 4,4'-dimethylbenzhydrol dissolved in 60 mL of dichloromethane. The reaction was allowed to stir for 30 minutes after the addition was complete. Thin layer chromatography (tlc) analysis after 30 minutes indicated a complete reaction. The product was transferred to a separatory funnel and washed two times with 70 mL of water. The dichloromethane layer was then dried with sodium sulfate, filtered, and evaporated. Yield: 40 g white solid. To one mole of ethylenediamine stirring at 0° C. was added dropwise a solution containing the 40 g of isolated product dissolved in 150 mL of dichloromethane. The reaction was then allowed to stir for 30 minutes after the addition was completed. The solution was then transferred to a separatory funnel and extracted four times with 100 mL of water. (The last wash contained a small amount of brine to minimize emulsion formation.) The dichloromethane layer was then dried with sodium sulfate, filtered and evaporated. Yield: 37.8 g clear yellow oil (101%) 1 H--NMR (CDCl3): δ=7.3-7.0 (dd, 8H), 6.7 (s, 1H), 5.5 (m,1H), 3.2-3.1 (dd, 2H), 2.8-2.7 (t, 2H), 2.3 (s, 6H), 1.1 (s, 2H)

Reference： [1]Current Patent Assignee: THERMO FISHER SCIENTIFIC INC - US6063569, 2000, A

23
[ 1336-21-6 ]
(S)-alloecgonine methyl ester [ No CAS ]
p-toluenenesulfonic acid monohydrate [ No CAS ]
[ 885-77-8 ]
(S)-(+)-2β-Carbomethoxy-3α-(di-4-methylphenylmethoxy)tropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With p-toluenesulfonic acid monohydrate In methanol; water; ethyl acetate; benzene	Resolution of (RS)-2-Carbomethoxy-3-tropinone (RS-2) (S)-Alloecgonine methyl ester (200 mg, 1.0 mmol), 4,4'-dimethylbenzhydrol (426 mg, 2.0 mmol), p-toluenesulfonic acid monohydrate (288 mg, 1.5 mmol) and benzene (50 mL) in a 100 mL round bottom flask fitted with Dean-Stark trap and condenser was heated at reflux for 18h. 4,4'-Dimethylbenzhydrol (200 mg) and p-toluenenesulfonic acid monohydrate (50 mg) were added and the reaction mixture was heated for another 5 h. Benzene was removed. The residue was dissolved in water (10 mL), basified with NH4 OH and extracted with CH2 Cl2 (2*50 mL). The dried (K2 CO3) extracts were concentrated to dryness. The residue was chromatographed with silica gel (2% NH4 OH, 3% MeOH in EtOAc) to afford (S)-(+)-2b-carbomethoxy-3a-(di-4-methylphenylmethoxy)tropane (316 mg, 80%) as a yellow viscous oil; Rf 0.70 (5% MeOH/EtOAc+NH4 OH); HCl salt: mp 156°-157° C. Anal. (C25 H31 NO3.HCl) C, H, N, Cl.

Reference： [1]Current Patent Assignee: HARVARD UNIVERSITY - US5506359, 1996, A

24
[ 142-08-5 ]
[ 885-77-8 ]
5-[bis(4-methylphenyl)methyl]pyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid at 180 - 250℃; for 2h;	8 A mixture of bis (4-methylphenyl) methanol (5 g) and pyridin-2 (IH) -one (6.72 g) was stirred at 180°C. To the solution was added concentrated H2SO4 (0.07 mL) , and the mixture was stirred at 2500C for 2 hours. Water (15 mL) and DCM (15 mL) were poured into the reaction mixture. The organic layer was washed with water and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane: EtOAc) . The desired fractions were collected and evaporated in vacuo, and the residue was washed with MeCN and dried in vacuo to give 5- [bis (4- methylphenyl) methyl] pyridin-2 ( IH) -one (0.94 g) as white crystals .1H-NMR (CDCl3)O: 2.32 ( 6H, s) , 5.19 (IH, s) , 6.50 (IH, d, J=9.4Hz) ,6.8 6(lH,d, J=2.6Hz) ,6.97 (4H, d, J=8. IHz) ,7.10 (4H, d, J=8. OHz) ,7.31-7.34 (IH, m) .MS(ESI, m/z) :312 (M+Na)+.
	With sulfuric acid at 180 - 250℃; for 2h;	5-[Bis(4-fluorophenyl)methyl]pyridin-2(1H)-one (6a) General procedure: The mixture of bis(4-fluorophenyl)methanol 5a (5.00 g, 22.7 mmol) and 2(1H)-pyridone (6.48 g, 68.1 mmol) was stirred at 180°C. Surfuric acid (60 μL) was added and stirred at 250°C for 2 hours.The mixture was cooled to room temperature, poured into water and extracted with dichloromethane. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified with silica gel column chromatography eluting with chloroform/methanol (gradient 100: 0 to 10: 1) to give amorphas. The amorphas was crystallized from acetonitrile to give 5-[bis(4-fluorophenyl)methyl]pyridin-2(1H)-one 6a (2.03 g, 30%) as white solid.

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - WO2008/72784, 2008, A1 Location in patent: Page/Page column 64-65
[2]Ito, Shinji; Terasaka, Tadashi; Zenkoh, Tatsuya; Matsuda, Hiroshi; Hayashida, Hisashi; Nagata, Hiroshi; Imamura, Yoshimasa; Kobayashi, Miki; Takeuchi, Makoto; Ohta, Mitsuaki [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1194 - 1197]

25
[ 885-77-8 ]
[ 98-88-4 ]
[ 69790-48-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 75℃; for 33h;

Reference： [1]Location in patent: experimental part Li, Hai-Hua; Dong, De-Jun; Tian, Shi-Kai [European Journal of Organic Chemistry, 2008, # 21, p. 3623 - 3626]

26
[ 5720-05-8 ]
[ 104-87-0 ]
[ 885-77-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With Rh<SUB>2</SUB>(trifluoroacetate)<SUB>4</SUB>(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)<SUB>2</SUB>; potassium <i>tert</i>-butylate In methanol at 65℃; for 3h; Inert atmosphere;
96.6%	With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; sodium hydroxide In water at 80℃; for 2h; Inert atmosphere;
91%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; tris(2,4-di-tert-butylphenyl)phosphite; potassium carbonate In 1,4-dioxane at 60℃; Glovebox; Inert atmosphere;	General procedure for Iridium (I)-catalyzed addition reactions of arylboronic acids with aldehydes: General procedure: In a glove-box with N2 atmosphere, [Ir(COD)Cl]2 (0.00125 mmol), tris(2,4-di-t-butylphenyl)phosphite 1 (0.0025 mmol) and 1,4-dioxane (0.2 mL) were placed in a vial. Then the vial containing the mixture was sealed and taken out of glove-box and heated in 110 oC of oil bath with stirring for 30 minutes. When the preparation of catalyst was completed, the vial was cooled to room temperature and brought into the glove-box again and followed by the addition of 1,4-dioxine (0.8 mL), aldehyde (0.25 mmol), arylboronic acids (0.375 mmol), and K2CO3 (0.75 mmol). After the mixture was stirred at 60 oC for 6-10 hours, the reaction was quenched by adding a small amount of water. Extraction with ethyl acetate followed by column chromatography on silica gel with ethyl acetate/hexane (v/v=1:10) afforded the alcohols.

89%	With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer In tetrahydrofuran; water at 20℃; for 19h;
71%	With potassium phosphate; platinacycle In toluene at 60 - 80℃;
	With potassium phosphate; platinacycle In toluene at 90 - 100℃; for 2h;

Reference： [1]Trindade, Alexandre F.; André, Vânia; Duarte, M. Teresa; Veiros, Luís F.; Gois, Pedro M.P.; Afonso, Carlos A.M. [Tetrahedron, 2010, vol. 66, # 44, p. 8494 - 8502]
[2]White, James R.; Price, Gareth J.; Plucinski, Pawel K.; Frost, Christopher G. [Tetrahedron Letters, 2009, vol. 50, # 52, p. 7365 - 7368]
[3]Liao, Yuan-Xi; Dong, Jie; Hu, Qiao-Sheng [Tetrahedron Letters, 2018, vol. 59, # 16, p. 1548 - 1550]
[4]Xing, Chun-Hui; Liu, Tao-Ping; Zheng, Jin Rong; Ng, Jaclynn; Esposito, Michelle; Hu, Qiao-Sheng [Tetrahedron Letters, 2009, vol. 50, # 35, p. 4953 - 4957]
[5]Liao, Yuan-Xi; Xing, Chun-Hui; He, Ping; Hu, Qiao-Sheng [Organic Letters, 2008, vol. 10, # 12, p. 2509 - 2512]
[6]Location in patent: scheme or table Liao, Yuan-Xi; Hu, Qiao-Sheng [Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 6986 - 6989]

27
[ 334474-15-6 ]
[ 885-77-8 ]
[ 1082852-36-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;

Reference： [1]Komeyama, Kimihiro; Takahashi, Keita; Takaki, Ken [Organic Letters, 2008, vol. 10, # 22, p. 5119 - 5122]

28
[ 885-77-8 ]
[ 100-51-6 ]
[ 1224874-55-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 60℃; for 12h; Green chemistry;
82%	With platinum on carbon at 130℃; for 1h; Neat (no solvent);

Reference： [1]Meng, Shan-Shui; Wang, Qian; Huang, Gong-Bin; Lin, Li-Rong; Zhao, Jun-Ling; Chan, Albert S. C. [RSC Advances, 2018, vol. 8, # 54, p. 30946 - 30949]
[2]Location in patent: experimental part Thiemann, Thies [Letters in Organic Chemistry, 2009, vol. 6, # 7, p. 515 - 525]

29
[ 875928-76-0 ]
[ 885-77-8 ]
[ 1233195-49-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 20℃; for 0.0833333h; Inert atmosphere;

Reference： [1]Wu, Lei; Shi, Min; Li, Yuxue [Chemistry - A European Journal, 2010, vol. 16, # 17, p. 5163 - 5172]

30
[ 288-88-0 ]
[ 885-77-8 ]
α-(1H-[1,2,4]triazol-1-yl)-(4,4'-dimethyl-diphenyl)-methane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4,4'-dimethylbenzhydrol With sulfuric acid In 1,2-dichloro-ethane at -10℃; for 1h; Stage #2: 1,2,4-Triazole In 1,2-dichloro-ethane at -10℃; for 3 - 4h;	3 Example - 3 Preparation of α - (IH-I, 2,4-Triazolyl) - 4,4'-dimethyIdiphenyImethane (Ha) A solution of 4,4'-dimethyl benzhydrol (25g, O.l lmol) in 1,2-dichloroethane (1000 ml) was cooled to -10 0C. and to it was added cone. Sulphuric acid (25 ml) drop-wise over a period of 30 minutes. The solution was stirred at this temperature for 30 min. more and added 1.2.4-triazole (25Og, 3,61 mol) in one lot. The reaction mixture was stirred for 3-4h.Unconsumed triazole was filtered out and the filtrate washed with (2x200ml) of water.The organic layer was dried over Anh. Sodium Sulphate and then concentrated on a rota- evaporator to give alpha (IH-I, 2,4-Triazolyl) - 4,4'-dimethyldiphenylmethane (28g).This was further purified by column chromatography (SiO2 60-120, Ethyl acetate: hexane). M.P. - 1010C.IR (KBr) (v Cm"1): 1513.5, 1431.6 IH NMR (CDCl3): δ 8.0 (s, IH), 7.9 (s, IH)5 7.25 - 7.15 (m, 4H), 7.02 - 7.00 (m, 4H) 6.68 (s, IH), 2.34 (s, 12H). Mass Spectrum: [M+Na], 286

Reference： [1]Current Patent Assignee: FRESENIUS SE & CO. KGAA - WO2007/74474, 2007, A1 Location in patent: Page/Page column 14; 16

31
[ 7677-24-9 ]
[ 885-77-8 ]
[ 92962-16-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With indium(III) bromide In dichloromethane at 20℃; Inert atmosphere;
98%	With indium(III) bromide In dichloromethane at 20℃; Inert atmosphere;
79%	With zinc trifluoromethanesulfonate In nitromethane at 100℃; for 16h; Inert atmosphere;

	With indium(III) chloride In dichloromethane at 20℃; for 13h; Inert atmosphere;
	Stage #1: 4,4'-dimethylbenzhydrol With molybdenum(V) chloride In dichloromethane at 23℃; for 0.25h; Stage #2: trimethylsilyl cyanide In dichloromethane at 23℃; for 3h;

Reference： [1]Wieteck, Marcel; Tokimizu, Yusuke; Rudolph, Matthias; Rominger, Frank; Ohno, Hiroaki; Fujii, Nobutaka; Hashmi, A. Stephen K. [Chemistry - A European Journal, 2014, vol. 20, # 49, p. 16331 - 16336]
[2]Plajer, Alex J.; Ahrens, Lukas; Wieteck, Marcel; Lustosa, Danilo M.; Babaahmadi, Rasool; Yates, Brian; Ariafard, Alireza; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K. [Chemistry - A European Journal, 2018, vol. 24, # 42, p. 10766 - 10772]
[3]Ebisawa, Kousuke; Izumi, Kana; Ooka, Yuka; Kato, Hiroaki; Kanazawa, Sayori; Komatsu, Sayura; Nishi, Eriko; Shigehisa, Hiroki [Journal of the American Chemical Society, 2020, vol. 142, # 31, p. 13481 - 13490]
[4]Mori, Keiji; Sueoka, Shosaku; Akiyama, Takahiko [Chemistry Letters, 2009, vol. 38, # 6, p. 628 - 629]
[5]Jiang, Hua-Jie; Liu, Kun; Yu, Jie; Zhang, Ling; Gong, Liu-Zhu [Angewandte Chemie - International Edition, 2017, vol. 56, # 39, p. 11931 - 11935][Angew. Chem., 2017, vol. 129, # 39, p. 12093 - 12097,5]

32
[ 106-38-7 ]
[ 104-88-1 ]
[ 885-77-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: para-bromotoluene With magnesium In tetrahydrofuran for 1h; Inert atmosphere; Stage #2: 4-chlorobenzaldehyde In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;

Reference： [1]Mori, Keiji; Sueoka, Shosaku; Akiyama, Takahiko [Chemistry Letters, 2009, vol. 38, # 6, p. 628 - 629]

33
[ 5084-80-0 ]
[ 104-87-0 ]
[ 885-77-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	With C₄₂H₆₂ClO₃PPd; sodium phosphate In toluene at 50℃; for 30h;	General procedure for palladacycle 1-catalyzed addition reactions of arylboroxines with aldehydes General procedure: To a vial containing aldehyde (0.25 mmol), arylboroxine (0.167 mmol), K3PO4 (0.75 mmol) and palladacycle 1 (0.00125-0.0000125 mmol) (palladacycle 1 was added in a toluene solution: 1 mg/mL solution of palladacycle 1 in toluene was freshly prepared and 1-40 μL of this solution was added to the reaction system by microsyringes) was added toluene (1 mL). After the mixture was stirred at 50-90 oC for 20-60 hours, the reaction was quenched by adding a small amount of water. Column chromatography on silica gel with ethyl acetate/hexane (v/v=1:10) afforded the alcohols.
83%	Stage #1: tri(4-tolyl)boroxine; 4-methyl-benzaldehyde With [2,2]bipyridinyl; sodium acetate; copper(l) chloride In o-xylene at 135℃; for 6h; Stage #2: With hydrogenchloride In o-xylene; water

Reference： [1]Liao, Yuan-Xi; Xing, Chun-Hui; Israel, Matthew; Hu, Qiao-Sheng [Tetrahedron Letters, 2011, vol. 52, # 26, p. 3324 - 3328]
[2]Location in patent: experimental part Liao, Yuan-Xi; Hu, Qiao-Sheng [Journal of Organic Chemistry, 2011, vol. 76, # 18, p. 7602 - 7607]

34
[ 123-75-1 ]
[ 885-77-8 ]
[ 252644-52-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium bicarbonate In thionyl chloride; acetonitrile	P.29 1-[bis(4-methylphenyl)methyl]pyrrolidine (Compound 29) 1-[bis(4-methylphenyl)methyl]pyrrolidine (Compound 29) Compound 14 (0.30 g, 1.41 mmol) was dissolved in thionyl chloride (1mL) (Wako Pure Chemical Industries, Ltd.), and the mixture was refluxed for 2 hours. The reaction solution was concentrated under reduced pressure, to thereby obtain a residue. The residue was dissolved in acetonitrile (5 mL) (Wako Pure Chemical Industries, Ltd.), and pyrrolidine (0.50 g, 7.03 mmol) was added thereto, and the mixture was refluxed for 2 hours and then allowed to cool to room temperature. A saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the reaction solution, and then mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.):methanol (Wako Pure Chemical Industries, Ltd.)=99:1 as an eluent), to thereby obtain the title compound (0.32 g, 84% yield). m.p. 61-63° C. 1H-NMR (CDCl3): δ1.74-1.78 (m, 4H), 2.40 (s, 6H), 2.35-2.45 (m, 4H), 4.01 (s, 1H), 7.05 (d, J=7.8 Hz, 4H), 7.32 (d, J=7.8 Hz, 4H). IR (cm-1): 2962, 2802, 1509, 721.
84%	Stage #1: 4,4'-dimethylbenzhydrol With thionyl chloride for 2h; Reflux; Stage #2: pyrrolidine In acetonitrile for 2h; Reflux;	29 Synthesis of 1-[bis(4-methylphenyl)methyl]pyrrolidine (Compound 29) Production Example 29 Synthesis of 1-[bis(4-methylphenyl)methyl]pyrrolidine (Compound 29) Compound 14 (0.30 g, 1.41 mmol) was dissolved in thionyl chloride (1) (Wako Pure Chemical Industries, Ltd.), and the mixture was refluxed for 2 hours. The reaction solution was concentrated under reduced pressure, to thereby obtain a residue. The residue was dissolved in acetonitrile (5 mL) (Wako Pure Chemical Industries, Ltd.), and pyrrolidine (0.50 g, 7.03 mmol) was added thereto, and the mixture was refluxed for 2 hours and then allowed to cool to room temperature. A saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the reaction solution, and then mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.):methanol (Wako Pure Chemical Industries, Ltd.)=99:1 as an eluent), to thereby obtain the title compound (0.32 g, 84% yield). m.p. 61-63° C. 1H-NMR (CDCl3): δ1.74-1.78 (m, 4H), 2.40 (s, 6H), 2.35-2.45 (m, 4H), 4.01 (s, 1H), 7.05 (d, J=7.8 Hz, 4H), 7.32 (d, J=7.8 Hz, 4H). IR (cm-1): 2962, 2802, 1509, 721.

Reference： [1]Current Patent Assignee: POLA ORBIS HOLDINGS INC - US2011/243865, 2011, A1
[2]Current Patent Assignee: POLA ORBIS HOLDINGS INC - US2015/328107, 2015, A1 Location in patent: Paragraph 0292 - 0296

35
[ 885-77-8 ]
[ 78-84-2 ]
[ 1353001-16-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With toluene-4-sulfonic acid In dibutyl ether at 50℃; for 24h;

Reference： [1]Xing, Chong; Sun, Hui; Zhang, Junmin; Li, Guohui; Chi, Yonggui Robin [Chemistry - A European Journal, 2011, vol. 17, # 44, p. 12272 - 12275]

36
[ 100-42-5 ]
[ 885-77-8 ]
[ 1352552-60-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With trifluorormethanesulfonic acid In ethylene dibromide at 60℃; Air atmosphere; stereoselective reaction;

Reference： [1]Location in patent: experimental part Yue, Hui-Lan; Wei, Wei; Li, Ming-Ming; Yang, Yong-Rong; Ji, Jian-Xin [Advanced Synthesis and Catalysis, 2011, vol. 353, # 17, p. 3139 - 3145]

37
[ 885-77-8 ]
[ 536-74-3 ]
[ 1353312-40-9 ]
(Z)-4,4'-(3-iodo-3-phenylprop-2-ene-1,1-diyl)bis(methylbenzene) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With iodine; iron; sodium iodide In ethylene dibromide at 55℃; optical yield given as %de;	2. General Procedure for the Synthesis of Alkenyl iodides General procedure: To a stirred solution of iron powder (0.5 mmol), iodine (0.5 mmol), sodium iodide (1.0 mmol) and alcohol (0.5 mmol) in DBE (1.0 mL) was added alkyne (1.5 mmol). The mixture was heated at 55°C and stirred for 8-12 h. Upon completion of the reaction, the mixture was filtered through a short column of silica gel and washed with ethyl acetate, and the solvents were removed by rotary evaporation to provide raw product. Then the product was purified on silica gel to afford the desired product.

Reference： [1]Li, Ming-Ming; Zhang, Qiang; Yue, Hui-Lan; Ma, Lei; Ji, Jian-Xin [Tetrahedron Letters, 2012, vol. 53, # 3, p. 317 - 319]

38
[ 128-39-2 ]
[ 885-77-8 ]
3,5-ditertiary-butyl-4-hydroxyphenyldi-p-tolylmethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 60℃; for 4h; Green chemistry;
	With sulfuric acid; acetic acid

Reference： [1]Meng, Shan-Shui; Wang, Qian; Huang, Gong-Bin; Lin, Li-Rong; Zhao, Jun-Ling; Chan, Albert S. C. [RSC Advances, 2018, vol. 8, # 54, p. 30946 - 30949]
[2]Location in patent: experimental part Nath, Naba K.; Nilapwar, Sanjay; Nangia, Ashwini [Crystal Growth and Design, 2012, vol. 12, # 3, p. 1613 - 1625]

39
[ 106-38-7 ]
[ 109-94-4 ]
[ 94-08-6 ]
[ 885-77-8 ]
[ 104-87-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 12% 2: 27% 3: 41%	Stage #1: para-bromotoluene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: formic acid ethyl ester In tetrahydrofuran; hexane at -78℃; for 3h; Stage #3: With ethanol; iodine; potassium carbonate In tetrahydrofuran; hexane at -78 - 20℃; for 14h;	4.2. Typical procedure for one-pot conversion of aromatic bromides into aromatic ethyl esters with ethyl formate General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3×20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77% yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil.

Reference： [1]Location in patent: experimental part Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo [Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709]

40
[ 885-77-8 ]
[ 106-49-0 ]
[ 1421841-88-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogenchloride; zinc(II) chloride In water at 160℃; for 1.5h; Inert atmosphere; Glovebox; Schlenk technique;
93%	With hydrogenchloride; zinc(II) chloride at 160℃;
89%	With hydrogenchloride; zinc(II) chloride at 160℃; for 1.5h;	Synthesis of the 2,6-bis(di-p-tolylmethyl)-4-methylaniline(TM-02): In a 250 mL round-bottomed flask, p-toluidine (6.75g, 63.0 mmol) and di-ptolylmethanol (TM-01) (25.7 g, 121 mmol) were stirred togetherat 160 °C until liquid. A solution of zinc chloride (4.22 g, 31.0 mmol) in HCl 36%(2.70 mL) was added dropwide to the reaction mixture. The flask was then openedto allow water evaporation, and stirring was continued at 160 °C untilsolidification of the reacting media (1.5 h). The residue was then allowed tocool to room temperature, dissolved in CH2Cl2 (300 mL), andwashed with NH4Cl aq. saturated solution and brine. The organiclayer was subsequently dried over K2CO3, and 20.0 g ofsilica gel was added to it. After filtration and concentration in vacuo, thecrude product was recrystallized from Ethyl acetate. The2,6-bis(di-p-tolylmethyl)-4-methylaniline (TM-02) was obtained as an off-white powder (26.9 g, 89%).1HNMR (CDCl3, 300 MHz)δ 7.07 (d, J = 7.9 Hz, 8H), 6.96 (d, J = 8.0 Hz, 8H), 6.38 (s, 2H), 5.36 (s,2H), 3.29 (s, 2H), 2.32 (s, 12H), 2.03 (s, 3H).

74%	With hydrogenchloride; zinc(II) chloride In water at 120 - 160℃; for 0.5h;	2,6-Bis(di-p-tolylmethyl)-4-methylaniline (A1). A mixture of p-Toluidine (1.44 g, 13.5 mmol, 1.0 equiv.) and Bis(3-methylphenyl)methanol (5.71 g, 27.0mmol, 2.0 equiv.) was heated to 120 °C. A solution of anhydrous zinc chloride (0.92 g, 6.8 mmol, 0.5equiv.) in concentrated hydrochloric acid (1.13 mL, 37% in H2O, 1.0 equiv.) was added to the mixture(exothermic + intense bubbling), and the temperature was raised to 160 °C. After 30 min at 160 °C, thereaction mixture was cooled to room temperature and dissolved in CH2Cl2 (200 mL). The CH2Cl2 layerwas washed with water (3×100 mL) and dried over anhydrous magnesium sulfate. The solution wasconcentrated to 20 mL. The product was crashed out with 200 ml methanol and washed with methanol (3 ×100 mL). The desired aniline was obtained as a white crystalline solid at 74.0 % (4.94 g) yield. 1H NMR(500 MHz, CDCl3) δ 7.07 (d, J = 7.9 Hz, 8H, aryl-H), 6.96 (d, J = 8.0 Hz, 8H, aryl-H), 6.38 (s, 2H, aryl-H),5.36 (s, 2H, CH(PhMe)2), 2.31 (s, 12H, CH(PhMe)2), 2.02 (s, 3H, Ar-CH3). 13C NMR (126 MHz, CDCl3) δ140.12, 139.73, 136.06, 129.59, 129.47, 129.27, 128.94, 126.62, 51.76 (CH(PhMe)2), 21.20 (CH(PhMe)2),21.16 (aryl-CH3). ESI-MS (m/z): calcd for C37H38N: 496.3004, found: 496.2997 [M+H]+. This compoundis previously known6.
74%	With hydrogenchloride; zinc(II) chloride In water at 120 - 160℃; for 0.5h; Inert atmosphere;
69.5%	With hydrogenchloride; zinc(II) chloride In water at 120 - 160℃; for 0.5h;	1.1.2 (2) The P-toluidine (1.44 g, 13.5 mmol, 1.0 equivalent) and b (methyl benzyl) methanol (5.71 g, 27.0 mmol, 2.0 equivalent) of the mixture is heated to 120 °C. Is added to the mixture of anhydrous zinc chloride (0.92 g, 6.8 mmol, 0.5 equivalent) of concentrated hydrochloric acid (1.13 ml, 37%, in H2In O, 1.0 equivalent) solution (exothermic + strong bubbling), the temperature is raised to 160 °C. In 160 °C under 30 minutes later, the reaction mixture is cooled to room temperature and dissolving in CH2Cl2(200 Ml) in. Water (3 × 100 ml) washing CH2Cl2Layer, and drying by anhydrous magnesium sulphate. The solution is concentrated to 20 ml. For the product 200 ml methanol washing and methanol (3 × 100 ml) washing. The desired aniline as a white crystalline solid, yield 74.0% (4.94 g).
	With hydrogenchloride; zinc(II) chloride In water

Reference： [1]Liu, Yu-Sheng; Harth, Eva [Angewandte Chemie - International Edition, 2021, vol. 60, # 45, p. 24107 - 24115][Angew. Chem., 2021, vol. 133, # 45, p. 24309 - 24317]
[2]Martin, Anthony R.; Chartoire, Anthony; Slawin, Alexandra M.Z.; Nolan, Steven P. [Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 1637 - 1643]
[3]Tian, Xiabing; Lin, Jing; Zou, Sheng; Lv, Junwei; Huang, Qingfei; Zhu, Jin; Huang, Shuping; Wang, Qiwei [Journal of Organometallic Chemistry, 2018, vol. 861, p. 125 - 130]
[4]Guo, Lihua; Kong, Wenyu; Xu, Yanjian; Yang, Yuliang; Ma, Rui; Cong, Li; Dai, Shengyu; Liu, Zhe [Journal of Organometallic Chemistry, 2018, vol. 859, p. 58 - 67]
[5]Gong, Yanfeng; Li, Shuaikang; Gong, Qi; Zhang, Shaojie; Liu, Binyuan; Dai, Shengyu [Organometallics, 2019, vol. 38, # 15, p. 2919 - 2926]
[6]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN109942638, 2019, A Location in patent: Paragraph 0037; 0042-0044
[7]Peng, Hongwei; Li, Shuaikang; Li, Gen; Dai, Shengyu; Ji, Mingjun; Liu, Zhe; Guo, Lihua [Applied Organometallic Chemistry, 2021, vol. 35, # 3]

41
[ 885-77-8 ]
[ 135248-89-4 ]
[ 1403825-57-9 ]

Yield	Reaction Conditions	Operation in experiment
52%	With trifluoroacetic acid at 25℃; for 1h;

Reference： [1]Gongora-Benitez, Miriam; Mendive-Tapia, Lorena; Ramos-Tomillero, Ivan; Breman, Arjen C.; Tulla-Puche, Judit; Albericio, Fernando [Organic Letters, 2012, vol. 14, # 21, p. 5472 - 5475,4] Góngora-Benítez, Miriam; Mendive-Tapia, Lorena; Ramos-Tomillero, Iván; Breman, Arjen C.; Tulla-Puche, Judit; Albericio, Fernando [Organic Letters, 2012, vol. 14, # 21, p. 5472 - 5475]

42
[ 885-77-8 ]
[ 1426391-61-8 ]
[ 1426391-39-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With iodine In dichloromethane at 25℃; for 0.75h;

Reference： [1]Jereb, Marjan; Vrazic, Dejan [Organic and Biomolecular Chemistry, 2013, vol. 11, # 12, p. 1978 - 1999]

43
[ 885-77-8 ]
[ 728-87-0 ]
[ 1426391-42-5 ]

Yield	Reaction Conditions	Operation in experiment
61%	With iodine In dichloromethane at 25℃; for 0.5h;

Reference： [1]Jereb, Marjan; Vrazic, Dejan [Organic and Biomolecular Chemistry, 2013, vol. 11, # 12, p. 1978 - 1999]

44
[ 106-38-7 ]
[ 109-94-4 ]
[ 885-77-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: para-bromotoluene With iodine; magnesium In tetrahydrofuran at 67℃; for 0.5h; Inert atmosphere; Reflux; Stage #2: formic acid ethyl ester In tetrahydrofuran at 20℃; for 2.25h; Inert atmosphere;
	Stage #1: para-bromotoluene With iodine; magnesium In tetrahydrofuran at 40℃; for 1h; Inert atmosphere; Stage #2: formic acid ethyl ester In tetrahydrofuran at 20 - 40℃; Inert atmosphere;	5 2.5 Synthesis of ditolylmethanol Ditolylmethanol was prepared by following a modified version of the previously reported procedure [23] . Magnesium turnings (1.87 g, 77 mmol) and a pinch of iodine were mixed in THF under N2 atmosphere followed by the addition of 4-bromotoluene (10.48 g, 59 mmol) at RT and heated (40 °C) for 1 h. After cooling this mixture to RT, ethyl formate (1.95 g, 26.5 mmol) and THF were added. The obtained solution was kept under heating (40 °C) for 30 min and overnight stirring at RT. To this, saturated NH4Cl solution was added and the organic part was extracted with CH2Cl2 to get an oily product. Upon trituration with petroleum ether, white crystals of ditolylmethanol was collected. M.p ≈ 81 °C. IR (KBr disc, cm-1): 3313 (br); 3100 (w); 3020 (w); 2910 (w); 1495 (s). 1H NMR (400 MHz, CDCl3): 7.3 (d, 4H, ArH), 5.8 (d, 1 H, JHH = 32 Hz, CH(OH)) 7.1 (d, 4H, ArH) 2.3 (s, 6H).
	Stage #1: para-bromotoluene With magnesium In tetrahydrofuran for 2h; Reflux; Stage #2: formic acid ethyl ester In tetrahydrofuran for 0.5h; Heating;	Synthesis of the di-ptolylmethanol(TM-01): A solution of 1-bromo-4-methylbenzene (10.0 g, 58.0 mmol) intetrahydrofuran (mL) was added dropwise to magnesium turnings (1.55 g, 64.0 mmol)under stirring. After two hours under reflux conditions, the reaction mixturewas cooled to room temperature. A solution of ethyl formate (2.00 g, 26.0 mol)in tetrahydrofuran (10 mL) was added dropwise. The reaction mixture was heatedfor another 30 min, cooled to room temperature, quenched with an aqueous NH4Clsolution (50 mL) and extracted with CH2Cl2 (3×50 mL). Thecombined organic layers were dried over MgSO4 and concentrated invacuo. The crude product was recrystallized from pentane.1HNMR (CDCl3, 300 MHz)δ 7.22 (d, J =7.2 Hz, 4H), 7.14 (d, J = 7.9 Hz, 4H), 5.79 (s, 1H), 2.33 (s,6H), 2.13 (s, 1H).

Reference： [1]Ammer, Johannes; Nolte, Christoph; Karaghiosoff, Konstantin; Thallmair, Sebastian; Mayer, Peter; Devivie-Riedle, Regina; Mayr, Herbert [Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14612 - 14630]
[2]Antony, Rajendran; Marimuthu, Rajendiran; Vishnoi, Pratap; Murugavel, Ramaswamy [Inorganica Chimica Acta, 2018, vol. 469, p. 173 - 182]
[3]Tian, Xiabing; Lin, Jing; Zou, Sheng; Lv, Junwei; Huang, Qingfei; Zhu, Jin; Huang, Shuping; Wang, Qiwei [Journal of Organometallic Chemistry, 2018, vol. 861, p. 125 - 130]

45
[ 885-77-8 ]
[ 68-11-1 ]
C₁₇H₁₈O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid at 20℃;
	With trifluoroacetic acid at 20℃;	1.2b Procedure B. Procedure B. Thioacetamides 2b-2f were synthesized in three steps. Step 1: Thioglycolic acid (1 equiv.) was reacted with diphenylmethanol or the appropriate substituted diphenylmethanol (1 equiv.) in TFA (14 equiv.) overnight at room temperature. After solvent removal in vacuo, the residue obtained was washed with water (5 mL) and hexanes (15 mL) to give the carboxylic acid product, which was carried to the next step without further purification. Step 2: The acid product from step 1 was reacted with K2C03 (1.5 equiv.) and iodomethane (CH3I; 1.5 equiv.) in acetone (50 mL) overnight under reflux conditions. After solvent removal in vacuo, the residue was suspended in water (20 mL) and extracted with CH2C12 (3 x 20 mL). The combined organic layer was dried over MgS04 and concentrated to give the methyl ester, which was carried to the next step without further purification. Step 3: A mixture of the ester (1 equiv.), NH4C1 (1.4 equiv.), concentrated NH4OH (28.0-30.0%; 20 mL) and MeOH (5.7 mL) was stirred at 50 °C for 72 hours. MeOH was removed in vacuo and the reaction mixture was diluted with water (50 mL), extracted with ethyl acetate (3 x 50 mL), and dried over Na2S04. The solvent was evaporated and the recovered crude product was purified by flash column chromatography using 1 : 1 ethyl acetate/hexanes to afford the pure product. 2-((Di-p-tolylmethyl)thio)acetamide (2b). Compound 2b was synthesized according to general procedure B to give 2b (450 mg, 52% yield) as a yellow oil. 1H NMR (CDC13): 5 7.26 -7.30 (m, 4H), 7.12 (d, J = 1.6 Hz, 4H), 6.54 (brs, 1H), 5.53 (brs, 1H), 5.11 (s, 1H), 3.07 (s, 2H), 2.31 (s, 6H); GC/MS (EI): m/z 285 (M+).

Reference： [1]Okunola-Bakare, Oluyomi M.; Cao, Jianjing; Kopajtic, Theresa; Katz, Jonathan L.; Loland, Claus J.; Shi, Lei; Newman, Amy Hauck [Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 1000 - 1013]
[2]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES - WO2014/138518, 2014, A2 Location in patent: Paragraph 0074; 0077

46
[ 79-36-7 ]
[ 885-77-8 ]
[ 1580541-48-5 ]

Yield	Reaction Conditions	Operation in experiment
78.9%	With pyridine In benzene at 20℃; for 12h; Inert atmosphere;

Reference： [1]Matic, Mirela; Denegri, Bernard; Kronja, Olga [European Journal of Organic Chemistry, 2014, vol. 2014, # 7, p. 1477 - 1486] Matic, Mirela; Denegri, Bernard; Kronja, Olga [European Journal of Organic Chemistry, 2014, vol. 2014, # 7, p. 1477 - 1486]

47
[ 885-77-8 ]
[ 76-02-8 ]
[ 1580541-53-2 ]

Yield	Reaction Conditions	Operation in experiment
63.1%	With pyridine In benzene at 20℃; for 12h; Inert atmosphere;

Reference： [1]Matic, Mirela; Denegri, Bernard; Kronja, Olga [European Journal of Organic Chemistry, 2014, vol. 2014, # 7, p. 1477 - 1486] Matic, Mirela; Denegri, Bernard; Kronja, Olga [European Journal of Organic Chemistry, 2014, vol. 2014, # 7, p. 1477 - 1486]

48
[ 885-77-8 ]
[ 536-74-3 ]
[ 1463500-96-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With indium(III) triflate In dichloromethane at 20 - 60℃;	General Procedure for Indium(III)-catalyzed DirectCoupling of Alcohols with Terminal Alkynes General procedure: Alcohol (0.25 mmol) was added to a mixture of alkyne(0.5 mmol) and In(OTf)3 (0.05 mmol) in DCE (1 mL) atroom temperature under air. The reaction mixture was stirredat 60 °C for 12-24 h. After cooling down to room temperatureand concentrating in vacuum, the residue was purifiedby silica-gel flash column chromatography using petroleumether/EtOAc as the eluent to give the desired product.

Reference： [1]Nan, Guangming; Zhou, Jun [Letters in Organic Chemistry, 2013, vol. 10, # 8, p. 555 - 561]

49
[ 885-77-8 ]
[ 766-83-6 ]
[ 1463501-03-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With indium(III) triflate In dichloromethane at 20 - 60℃;	General Procedure for Indium(III)-catalyzed DirectCoupling of Alcohols with Terminal Alkynes General procedure: Alcohol (0.25 mmol) was added to a mixture of alkyne(0.5 mmol) and In(OTf)3 (0.05 mmol) in DCE (1 mL) atroom temperature under air. The reaction mixture was stirredat 60 °C for 12-24 h. After cooling down to room temperatureand concentrating in vacuum, the residue was purifiedby silica-gel flash column chromatography using petroleumether/EtOAc as the eluent to give the desired product.

Reference： [1]Nan, Guangming; Zhou, Jun [Letters in Organic Chemistry, 2013, vol. 10, # 8, p. 555 - 561]

50
[ 67237-53-0 ]
[ 885-77-8 ]
[ 1463501-07-6 ]

Yield	Reaction Conditions	Operation in experiment
37%	With indium(III) triflate In dichloromethane at 20 - 60℃;	General Procedure for Indium(III)-catalyzed DirectCoupling of Alcohols with Terminal Alkynes General procedure: Alcohol (0.25 mmol) was added to a mixture of alkyne(0.5 mmol) and In(OTf)3 (0.05 mmol) in DCE (1 mL) atroom temperature under air. The reaction mixture was stirredat 60 °C for 12-24 h. After cooling down to room temperatureand concentrating in vacuum, the residue was purifiedby silica-gel flash column chromatography using petroleumether/EtOAc as the eluent to give the desired product.

Reference： [1]Nan, Guangming; Zhou, Jun [Letters in Organic Chemistry, 2013, vol. 10, # 8, p. 555 - 561]

51
[ 885-77-8 ]
[ 536-74-3 ]
[ 1616471-06-7 ]
[ 1616471-07-8 ]

Yield	Reaction Conditions	Operation in experiment
66 % de	With tetrafluoroboric acid In ethylene dibromide at 55℃; Overall yield = 49 %;	2. General Procedure for the Synthesis of fluoroalkenes General procedure: To a stirred solution of alcohol (0.5 mmol) andfluoroboric acid (0.75mmol)in DBE (2.0 mL) was added alkyne (0.6 mmol). The mixture was heated at 55°C andstirred for 8-10 h. Upon completion of the reaction, the solvent was removed by rotary evaporation to provide rawproduct, which waspurified on silica gel to afford themixture of E/Z isomers.

Reference： [1]Yan, Xiao-Wei; Zhang, Qiang; Wei, Wei; Ji, Jian-Xin [Tetrahedron Letters, 2014, vol. 55, # 28, p. 3750 - 3752]

52
[ 885-77-8 ]
[ 622-76-4 ]
[ 1616470-98-4 ]
[ 1616470-99-5 ]

Yield	Reaction Conditions	Operation in experiment
82 % de	With tetrafluoroboric acid In ethylene dibromide at 55℃; Overall yield = 45 %;	2. General Procedure for the Synthesis of fluoroalkenes General procedure: To a stirred solution of alcohol (0.5 mmol) andfluoroboric acid (0.75mmol)in DBE (2.0 mL) was added alkyne (0.6 mmol). The mixture was heated at 55°C andstirred for 8-10 h. Upon completion of the reaction, the solvent was removed by rotary evaporation to provide rawproduct, which waspurified on silica gel to afford themixture of E/Z isomers.

Reference： [1]Yan, Xiao-Wei; Zhang, Qiang; Wei, Wei; Ji, Jian-Xin [Tetrahedron Letters, 2014, vol. 55, # 28, p. 3750 - 3752]

53
[ 624-31-7 ]
[ 104-87-0 ]
[ 885-77-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With diphenyl hydrogen phosphate; [Ni(dipy)(μ-Cl)2]; diisopropylamine; sodium iodide; zinc In hexane at 95℃; for 7h; Inert atmosphere; Sealed tube;
53%	Stage #1: 4-tolyl iodide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran; hexane at -78℃; for 0.5h;
53%	Stage #1: 4-tolyl iodide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran; hexane at -78℃; for 0.5h;

Stage #1: 4-tolyl iodide With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran at -78 - 20℃; Inert atmosphere;

Reference： [1]Ishida, Seima; Suzuki, Hiroyuki; Uchida, Seiichiro; Yamaguchi, Eiji; Itoh, Akichika [European Journal of Organic Chemistry, 2019, vol. 2019, # 45, p. 7483 - 7487]
[2]Wieteck, Marcel; Tokimizu, Yusuke; Rudolph, Matthias; Rominger, Frank; Ohno, Hiroaki; Fujii, Nobutaka; Hashmi, A. Stephen K. [Chemistry - A European Journal, 2014, vol. 20, # 49, p. 16331 - 16336]
[3]Plajer, Alex J.; Ahrens, Lukas; Wieteck, Marcel; Lustosa, Danilo M.; Babaahmadi, Rasool; Yates, Brian; Ariafard, Alireza; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K. [Chemistry - A European Journal, 2018, vol. 24, # 42, p. 10766 - 10772]
[4]Maiti, Debabrata; Halder, Atreyee; De Sarkar, Suman [Advanced Synthesis and Catalysis, 2019, vol. 361, # 21, p. 4941 - 4948]

54
[ 885-77-8 ]
[ 135-19-3 ]
1-(di-p-tolylmethyl)naphthalen-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With stannic bromide In dichloromethane at 20℃; for 24h; Inert atmosphere;	Typical Procedure for Friedel-Crafts Type Dehydrative Alkylation Reaction of Benzhydrol (1a) with 2-Naphthol (Table 1, entry 5): General procedure: To a solution of SnBr4 (2.7 mg. 6.16 μmol) in CH2Cl2 (1.3 mL) at room temperature wassuccessively added benzhydrol (1a) (22.6 mg. 0.123 mmol), and 2-naphthol (28.3 mg, 0.196mmol). The reaction mixture was stirred for 24 h at room temperature and then it was quenchedwith saturated aqueous NaHCO3 at 0 °C. The organic layer was separated and the aqueous layerwas extracted with CH2Cl2. The combined organic layer was dried over Na2SO4. After filtrationof the mixture and evaporation of the solvent, the crude product was purified by preparative thinlayer chromatography on silica (toluene) to afford the desired compound 2a (36.6 mg, 96%yield) as a pale-brownish solid.

Reference： [1]Suzuki, Nobuharu; Tsuchihashi, Shiori; Nakata, Kenya [Tetrahedron Letters, 2016, vol. 57, # 13, p. 1456 - 1459]

55
C₁₉H₂₃NOS [ No CAS ]
[ 19226-36-9 ]
[ 885-77-8 ]
7-methyl-2-phenyl-4-<i>p</i>-tolyl-quinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: C₁₉H₂₃NOS; 3-phenyl-5H-1,4,2-dioxazol-5-one With carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; silver(I) triflimide In 1,2-dichloro-ethane at 120℃; for 16h; Inert atmosphere; Sealed tube; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 0.5h; Inert atmosphere; Sealed tube;

Reference： [1]Wang, Fen; Wang, He; Wang, Qiang; Yu, Songjie; Li, Xingwei [Organic Letters, 2016, vol. 18, # 6, p. 1306 - 1309]

56
[ 885-77-8 ]
[ 56866-32-1 ]
2-((5-methyl-3-phenyl-1-(p-tolyl)-2,3-dihydro-1H-inden-2-yl)methyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With iron(III) chloride hexahydrate In 1,2-dichloro-ethane at 120℃; for 2h; Inert atmosphere; stereoselective reaction;

Reference： [1]Li, Yali; Zhang, Lingjuan; Zhang, Zongyao; Xu, Jianbin; Pan, Yixiao; Xu, Conghui; Liu, Lingxian; Li, Zengguang; Yu, Zhiyong; Li, Huanrong; Xu, Lijin [Advanced Synthesis and Catalysis, 2016, vol. 358, # 13, p. 2148 - 2155]

57
[ 885-77-8 ]
[ 104-94-9 ]
2,6-bis(di-p-tolylmethyl)-4-methoxyaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.2%	With hydrogenchloride; zinc(II) chloride In water at 120 - 160℃; for 0.5h;	2,6-Bis(di-p-tolylmethyl)-4-methylaniline (A1). General procedure: A mixture of p-Toluidine (1.44 g, 13.5 mmol, 1.0 equiv.) and Bis(3-methylphenyl)methanol (5.71 g, 27.0mmol, 2.0 equiv.) was heated to 120 °C. A solution of anhydrous zinc chloride (0.92 g, 6.8 mmol, 0.5equiv.) in concentrated hydrochloric acid (1.13 mL, 37% in H2O, 1.0 equiv.) was added to the mixture(exothermic + intense bubbling), and the temperature was raised to 160 °C. After 30 min at 160 °C, thereaction mixture was cooled to room temperature and dissolved in CH2Cl2 (200 mL). The CH2Cl2 layerwas washed with water (3×100 mL) and dried over anhydrous magnesium sulfate. The solution wasconcentrated to 20 mL. The product was crashed out with 200 ml methanol and washed with methanol (3 ×100 mL). The desired aniline was obtained as a white crystalline solid at 74.0 % (4.94 g) yield.
	With hydrogenchloride; zinc(II) chloride In water at 160℃;
	With hydrogenchloride; zinc(II) chloride In water at 160℃;

Reference： [1]Guo, Lihua; Kong, Wenyu; Xu, Yanjian; Yang, Yuliang; Ma, Rui; Cong, Li; Dai, Shengyu; Liu, Zhe [Journal of Organometallic Chemistry, 2018, vol. 859, p. 58 - 67]
[2]Okumura, Shogo; Tang, Shuwei; Saito, Teruhiko; Semba, Kazuhiko; Sakaki, Shigeyoshi; Nakao, Yoshiaki [Journal of the American Chemical Society, 2016, vol. 138, # 44, p. 14699 - 14704]
[3]Ma, Bei-Bei; Lan, Xiao-Bing; Shen, Dong-Sheng; Liu, Feng-Shou; Xu, Chang [Journal of Organometallic Chemistry, 2019, vol. 897, p. 13 - 22]

58
[ 392-56-3 ]
[ 885-77-8 ]
4,4′-((perfluorophenoxy)methylene)bis(methylbenzene) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	Stage #1: Hexafluorobenzene With potassium In tetrahydrofuran at 60℃; Inert atmosphere; Solvolysis; Stage #2: 4,4'-dimethylbenzhydrol In tetrahydrofuran for 1.5h; Inert atmosphere; Heating; Solvolysis;	4,4'-Dimethylbenzhydryl Pentafluorophenyl Ether. Freshly cut potassium (0.15 g; 3.8 mmol) was added to the previously prepared stirring solution of hexafluorobenzene(0.70 g, 3.8 mmol) in anhydrous tetrahydrofurane (15 ml),and the solution was stirred at 60 °C for few minutes under an atmosphere of argon. The solution of 4,4'-dimethylbenzhydrol(0.80 g, 3.8 mmol) in tetrahydrofurane (10 ml) was then added dropwise with vigorously stirring, and the reaction mixture was heated further for 1.5 h. A brown precipitate was filtered off, excess of potassium was removed, and then 15 ml of benzene was added in the solution. After that, the organic layer was washed with water (3 × 15 ml) and dried over anhydrous sodium sulfate.The solvent was removed in vacuo and the residue was then left in a freezer with 10 ml of hexane for 12 h. After removal of white crystals, 0.30 g of pale-yellow oil was obtained (49.0 %); 1H NMR (400 MHz, CDCl3, 20 °C): δ/ppm= 2.32 (s, 6H; Ar-CH3), 6.31 (s, 1H; Ar2CH), 7.13 (d, J = 7.9 Hz,4H; ArH), 7.29 (d, J = 8.1 Hz, 4H; ArH); 13C NMR (150 MHz,CDCl3, 20 °C): δ/ppm = 21.2 (Ar-CH3), 87.0 (Ar2CH), 127.1,129.2, 136.7, 138.3 (Ar); 19F NMR (282 MHz, CDCl3, 20 °C):δ/ppm = -154.2 (d, JFF = 25.4 Hz, 2F; F5Ar), -163.0 (t, JFF =44.1 Hz, 1F; F5Ar), -163.6 (t, JFF = 40.1 Hz, 2F; F5Ar).

Reference： [1]Matić, Mirela; Bebek, Nives; Denegri, Bernard; Kronja, Olga [Croatica Chemica Acta, 2016, vol. 89, # 3, p. 355 - 362]

59
[ 885-77-8 ]
[ 95-71-6 ]
2-(di-p-tolylmethyl)-5-methylbenzene-1,4-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With toluene-4-sulfonic acid; In water; at 40℃; for 1h;Green chemistry;	General procedure: A mixture of hydroquinones 1 (0.5 mmol), TsOH.H2O (2 mol%) and benzhydryl alcohols 2(0.6 mmol) in H2O (2 mL) was heated at 40 C for 1h. After it was cooled, the reactionmixture was poured into water and extracted with EtOAc. The organic layer was dried overanhyd. Na2SO4, and concentrated in a rotatory evaporator. The residue was purified by silicagel column chromatography (step gradient with 10-20% ethyl acetate in hexanes as theeluent) to afford the desired products 3 and 4.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2813 - 2817

60
[ 885-77-8 ]
[ 824-46-4 ]
2-(di-p-tolylmethyl)-5-methoxybenzene-1,4-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With toluene-4-sulfonic acid In water at 40℃; for 1h; Green chemistry;	General procedure for the synthesis of benzylated hydroquinones: General procedure: A mixture of hydroquinones 1 (0.5 mmol), TsOH.H2O (2 mol%) and benzhydryl alcohols 2(0.6 mmol) in H2O (2 mL) was heated at 40 °C for 1h. After it was cooled, the reactionmixture was poured into water and extracted with EtOAc. The organic layer was dried overanhyd. Na2SO4, and concentrated in a rotatory evaporator. The residue was purified by silicagel column chromatography (step gradient with 10-20% ethyl acetate in hexanes as theeluent) to afford the desired products 3 and 4.

Reference： [1]Singh, Pallavi; Singh, Udai Pratap; Peddinti, Rama Krishna [Tetrahedron Letters, 2017, vol. 58, # 29, p. 2813 - 2817]

61
[ 885-77-8 ]
[ 1079-21-6 ]
4-(di-p-tolylmethyl)-[1,1’-biphenyl]-2,5-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With toluene-4-sulfonic acid In water at 40℃; for 1h; Green chemistry;	General procedure for the synthesis of benzylated hydroquinones: General procedure: A mixture of hydroquinones 1 (0.5 mmol), TsOH.H2O (2 mol%) and benzhydryl alcohols 2(0.6 mmol) in H2O (2 mL) was heated at 40 °C for 1h. After it was cooled, the reactionmixture was poured into water and extracted with EtOAc. The organic layer was dried overanhyd. Na2SO4, and concentrated in a rotatory evaporator. The residue was purified by silicagel column chromatography (step gradient with 10-20% ethyl acetate in hexanes as theeluent) to afford the desired products 3 and 4.

Reference： [1]Singh, Pallavi; Singh, Udai Pratap; Peddinti, Rama Krishna [Tetrahedron Letters, 2017, vol. 58, # 29, p. 2813 - 2817]

62
[ 7693-45-0 ]
[ 885-77-8 ]
4,4'-dimethylbenzhydryl 4-chlorophenyl carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With pyridine In benzene at 20℃; Inert atmosphere;

Reference： [1]Matić, Mirela; Katić, Matija; Denegri, Bernard; Kronja, Olga [Journal of Organic Chemistry, 2017, vol. 82, # 15, p. 7820 - 7831]

63
[ 1569-69-3 ]
[ 885-77-8 ]
cyclohexyl[di(p-tolyl)methyl]sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.0166667h;	Symmetrical and Unsymmetrical Diarylmethyl Thioethers; General Procedure General procedure: To a solution of thiol 1 (0.5 mmol) in anhyd CH2Cl2 (2 mL) was added diaryl carbinol 2 (0.6 mmol) and BF3*OEt2 (5 mol% solution in CH2Cl2; 1 mL). The reaction mixture was stirred vigorously for <1 min. After completion of the reaction as checked by TLC, the solvent was removed under reduced pressure, and the residue was subjected to silica gel column chromatography by using 5-10% EtOAc in hexanes to afford the desired symmetrical and unsymmetrical diarylmethyl thioether in good to quantitative yield.