Name: 2235-01-0|Dimethoxydiphenylmethane|98% GC
Brand: Ambeed
SKU: A614962
Price: 17.0 USD
Availability: InStock
Rating: 91 (35 reviews)

1
[ 67-56-1 ]
[ 2051-90-3 ]
[ 2235-01-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With pyridine at 0 - 20℃; for 2h;
	With sodium azide
	With pyridine at 0℃;

With sodium methylate

Reference： [1]Schmidt, Matthias; Ungvari, Johannes; Gloede, Julia; Dobner, Bodo; Langner, Andreas [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 6, p. 2283 - 2297]
[2]Schroeter [Chemische Berichte, 1909, vol. 42, p. 2346][Chemisches Zentralblatt, 1910, vol. 81, # I, p. 1470]
[3]Straus; Ecker [Chemische Berichte, 1906, vol. 39, p. 2995]
[4]Papadakis [Journal of the American Chemical Society, 1936, vol. 58, p. 665]
[5]Razus, Alexandru C.; Gheorghiu, Mircea D.; Bartha, Emeric [Revue Roumaine de Chimie, 1991, vol. 36, # 1-3, p. 215 - 228]

2
[ 2235-01-0 ]
[ 599-67-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With lithium In tetrahydrofuran Ambient temperature;
	With 1,4-dioxane; lithium anschliessendes Behandeln mit Methanol;
	With tetrahydrofuran; lithium anschliessendes Behandeln mit Methanol;

	With 1,4-dioxane; sodium anschliessendes Behandeln mit Methanol;
	With diethyl ether; sodium Einw_. von Alkohol oder von Kohlendioxyd;
	With tetrahydrofuran; sodium anschliessendes Behandeln mit Methanol;
	Multi-step reaction with 2 steps 1: potassium; THF / anschliessend Behandeln mit HgCl₂ 2: potassium; THF / anschliessend Behandeln mit Methanol

Reference： [1]Azzena; Melloni; Pisano; Sechi [Tetrahedron Letters, 1994, vol. 35, # 36, p. 6759 - 6762]
[2]Wittig; Happe [Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 205,208, 216]
[3]Wittig; Happe [Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 205,208, 216]
[4]Wittig; Happe [Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 205,208, 216]
[5]Schlenk; Bergmann [Justus Liebigs Annalen der Chemie, 1928, vol. 464, p. 28]
[6]Wittig; Happe [Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 205,208, 216]
[7]Wittig; Schloer [Suomen Kemistilehti B, 1958, vol. 31, p. 2,7]

3
[ 2235-01-0 ]
[ 101-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; palladium; acetic acid Hydrogenolyse;
92.3 % Chromat.	With triethylsilane; Nafion-H (perfluororesinsulfonic acid) In dichloromethane for 4h; Heating;

Reference： [1]Papadakis [Journal of the American Chemical Society, 1936, vol. 58, p. 665]
[2]Olah, George A.; Yamato, Takehiko; Iyer, Pradeep; Prakash, G.K. Surya [Journal of Organic Chemistry, 1986, vol. 51, # 14, p. 2826 - 2828]

4
[ 2235-01-0 ]
[ 985-93-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrahydrofuran; potassium anschliessend Behandeln mit HgCl₂;
	With lithium aluminium tetrahydride; titanium tetrachloride In tetrahydrofuran

Reference： [1]Wittig; Schloer [Suomen Kemistilehti B, 1958, vol. 31, p. 2,7]
[2]Ishikawa,H.; Mukaiyama,T. [Bulletin of the Chemical Society of Japan, 1978, vol. 51, p. 2059 - 2063]

5
[ 2235-01-0 ]
[ 131866-04-1 ]

Yield	Reaction Conditions	Operation in experiment
	With glycerol at 250℃;

Reference： [1]Blicke; Schumann [Journal of the American Chemical Society, 1952, vol. 74, p. 2613]

6
[ 504-24-5 ]
[ 2235-01-0 ]
[ 36728-58-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With 4 A molecular sieve; scandium tris(trifluoromethanesulfonate) In xylene for 96h; Heating;
32%	at 200℃; for 96h;

Reference： [1]Heaney, Harry; Simcox, Michael T.; Slawin, Alexandra M.Z.; Giles, Robert G. [Synlett, 1998, # 6, p. 640 - 642]
[2]Desbene, P. L.; Jehanno, N. [Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1313 - 1319]

7
[ 67-56-1 ]
[ 119-61-9 ]
[ 2235-01-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With trimethyl orthoformate for 6h; Heating;
88%	With formylmorpholine-dimethylsulfate-adduct for 36h; Ambient temperature;
80%	With trimethyl orthoformate In dichloromethane at 20℃; for 120h;

53%	With toluene-4-sulfonic acid at 20℃; for 16h;	Benzophenone Dimethyl Acetal (1g).⁶ p-Toluenesulfonic acid (0.48 g, 2.5 mmol) was added to a mixture of benzophenone (9.1 g, 50 mmol) and methanol (75 mL). The reaction mixture was stirred at RT for 16 h, followed by filtration on funnel by suction. The crude product was recrystallized from methanol and dried in a vacuum, affording dimethyl acetal 1g (6.0 g, 53 % yield)
	With toluene-4-sulfonic acid; 2,2-dimethoxy-propane
	at 20℃; for 10h; atmospheric pressure;

Reference： [1]Mansilla, Horacio; Afonso, Maria M. [Synthetic Communications, 2008, vol. 38, # 15, p. 2607 - 2618]
[2]Kantlehner, Willi; Gutbrod, Heinz-Dieter; Funke, Bernd [Liebigs Annalen der Chemie, 1980, # 2, p. 246 - 252]
[3]Suelue, Mustafa; Venanzi, Luigi M. [Helvetica Chimica Acta, 2001, vol. 84, # 4, p. 898 - 907]
[4]Takehira, Satoshi; Masui, Yoichi; Onaka, Makoto [Chemistry Letters, 2014, vol. 43, # 4, p. 498 - 500]
[5]Hardie,W.R. et al. [Journal of Medicinal Chemistry, 1966, vol. 9, p. 127 - 136]
[6]Thomas, Bejoy; Sugunan [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2005, vol. 44, # 7, p. 1345 - 1354]

8
[ 67-56-1 ]
[ 908093-98-1 ]
[ 2235-01-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 1h;
87%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 1h;
85%	In tetrahydrofuran at 30℃; for 6h;

(i) indan-1,2,3-trione, 1,2-dimethoxy-ethane, (ii) /BRN= 779235/; Multistep reaction;

Reference： [1]Oshima, Takumi; Nishioka, Ryoji; Nagai, Toshikazu [Tetrahedron Letters, 1980, vol. 21, p. 3919 - 3922]
[2]Oshima, Takumi; Nagai, Toshikazu [Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 7, p. 2039 - 2044]
[3]Oshima, Takumi; Nagai, Toshikazu [Bulletin of the Chemical Society of Japan, 1980, vol. 53, # 11, p. 3284 - 3288]
[4]Schoenberg,A.; Singer,E. [Chemische Berichte, 1972, vol. 105, p. 2246 - 2257]

9
[ 31469-15-5 ]
[ 2235-01-0 ]
[ 94123-64-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With trimethylsilyl cyanide In acetonitrile for 3h; Ambient temperature;

Reference： [1]Soga, Tsunehiko; Takenoshita, Haruhiro; Yamada, Masaaki; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 11, p. 3122 - 3131]

10
[ 608-68-4 ]
[ 2235-01-0 ]
[ 146499-09-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With toluene-4-sulfonic acid In cyclohexane Heating;
82%	With toluene-4-sulfonic acid In benzene Heating;
66%	With toluene-4-sulfonic acid In toluene Reflux;

60%	With toluene-4-sulfonic acid In benzene at 80℃;
	With toluene-4-sulfonic acid In methanol; benzene Heating;

Reference： [1]Seebach, Dieter; Beck, Albert K.; Dahinden, Robert; Hoffmann, Matthias; Kuehnle, Florian N. M. [Croatica Chemica Acta, 1996, vol. 69, # 2, p. 459 - 484]
[2]Irrure, J.; Alonso-Alija, C.; Piniella, J. F.; Alvarez-Larena, A. [Tetrahedron Asymmetry, 1992, vol. 3, # 12, p. 1591 - 1596]
[3]Shim, You-Jin; Choi, Kihang [Organic Letters, 2010, vol. 12, # 4, p. 880 - 882]
[4]Gerard, Baudouin; Sangji, Sheharbano; O'Leary, Daniel J.; Porco Jr., John A. [Journal of the American Chemical Society, 2006, vol. 128, # 24, p. 7754 - 7755]
[5]Altava, Belen; Burguete; Garcia-Verdugo, Eduardo; Luis, Santiago V.; Miravet, Juan F.; Vicent, Maria J. [Tetrahedron Asymmetry, 2000, vol. 11, # 24, p. 4885 - 4893]

11
[ 7677-24-9 ]
[ 2235-01-0 ]
[ 125288-37-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With Fe-montmorillonite In dichloromethane at 0℃; for 2h;
94%	In dichloromethane for 24h; Ambient temperature;
94%	In dichloromethane for 24h; Ambient temperature;

Reference： [1]Higuchi, Katsumi; Onaka, Makoto; Izumi, Yusuke [Bulletin of the Chemical Society of Japan, 1993, vol. 66, # 7, p. 2016 - 2032]
[2]Soga, Tsunehiko; Takenoshita, Haruhiro; Yamada, Masaaki; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 11, p. 3122 - 3131]
[3]Mukaiyama, Teruaki; Soga, Tsunehiko; Takenoshita, Haruhiro [Chemistry Letters, 1989, p. 997 - 1000]

12
[ 5350-57-2 ]
[ 101-81-5 ]
[ 1016-09-7 ]
[ 2235-01-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 3 % Chromat. 2: 32 % Chromat. 3: 37%	With sodium methylate In methanol at 70℃; for 6.4h; C-anode, C-cathode, 4.4 F/mol, constant current 0.5 A, undivided cell;

Reference： [1]Chiba, Toshiro; Okimoto, Mitsuhiro; Nagai, Hiroshi; Takata, Yoshiyuki [Journal of Organic Chemistry, 1983, vol. 48, # 18, p. 2968 - 2972]

13
[ 2235-01-0 ]
[ 72658-09-4 ]
[ 343947-10-4 ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylsilyl cyanide In acetonitrile for 3h; Ambient temperature; Yield given. Yields of byproduct given;

Reference： [1]Soga, Tsunehiko; Takenoshita, Haruhiro; Yamada, Masaaki; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 11, p. 3122 - 3131]

14
[ 2235-01-0 ]
[ 17325-85-8 ]
[ 139132-83-5 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In isopropyl alcohol for 0.166667h; Heating; Yield given;

Reference： [1]Thurkauf; Mattson; Richardson; Mirsadeghi; Ornstein; Harrison Jr.; Rice; Jacobson; Monn [Journal of Medicinal Chemistry, 1992, vol. 35, # 8, p. 1323 - 1329]

15
[ 2235-01-0 ]
[ 6577-25-9 ]
2-(2,2-Diphenyl-[1,3]dioxan-5-yl)-piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In isopropyl alcohol for 0.333333h; Heating;

Reference： [1]Thurkauf; Mattson; Richardson; Mirsadeghi; Ornstein; Harrison Jr.; Rice; Jacobson; Monn [Journal of Medicinal Chemistry, 1992, vol. 35, # 8, p. 1323 - 1329]

16
[ 2235-01-0 ]
2-(tert-butyldimethylsilyl)oxy-10-<(tert-butyldimethylsilyl)oxy>methyl-8,9-dihydroxy-7-methyl-7,8,9,10-tetrahydrophenanthridine [ No CAS ]
(7R,7aS,10aR,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-9,9-diphenyl-7,7a,10a,11-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sulfuric acid In dichloromethane at 40℃; for 2h;
83%	With sulfuric acid In dichloromethane at 40℃;

Reference： [1]Yoon, Taeyoung; Shair, Matthew D.; Danishefsky, Samuel J.; Shulte, Gayle K. [Journal of Organic Chemistry, 1994, vol. 59, # 14, p. 3752 - 3754]
[2]Danishefsky, Samuel J.; Shair, Matthew D. [Journal of Organic Chemistry, 1996, vol. 61, # 1, p. 16 - 44]

17
[ 2235-01-0 ]
[ 119-61-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With water In acetone for 0.5h;
100%	With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 1h; Ambient temperature;
99%	In water at 30℃; for 0.5h;

99%	With water at 120℃; for 0.5h; microwave irradiation;
95%	In methanol; water for 1h; Heating;
94%	With Methyltrichlorosilane; sodium iodide In acetonitrile for 12h; Ambient temperature;
94%	With Methyltrichlorosilane; sodium iodide In acetonitrile for 12h; Ambient temperature; var. dimethyl ketals;
93%	With chloro-trimethyl-silane; samarium(III) chloride In tetrahydrofuran for 30h; Ambient temperature;
91%	In water at 100℃; for 1.58333h;
	Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / chloroform / 12 h / Sealed tube 2: urea hydrogen peroxide adduct / water-d2; aq. phosphate buffer; [D₃]acetonitrile / pH 8
	Multi-step reaction with 2 steps 1: hydrogen; palladium on activated charcoal / methanol 2: urea hydrogen peroxide adduct / [D₃]acetonitrile / pH 8

Reference： [1]Olah, George A.; Narang, Subhash C.; Meidar, David; Salem, George F. [Synthesis, 1981, # 4, p. 282 - 283]
[2]Tanemura, Kiyoshi; Suzuki, Tsuneo; Horaguchi, Takaaki [Journal of the Chemical Society. Chemical communications, 1992, # 14, p. 979 - 980]
[3]Chang, Chih-Ching; Liao, Bei-Sih; Liu, Shiuh-Tzung [Synlett, 2007, # 2, p. 283 - 287]
[4]Procopio, Antonio; Gaspari, Marco; Nardi, Monica; Oliverio, Manuela; Tagarelli, Antonio; Sindona, Giovanni [Tetrahedron Letters, 2007, vol. 48, # 49, p. 8623 - 8627]
[5]Ranu, Brindaban C.; Jana, Ranjan; Samanta, Sampak [Advanced Synthesis and Catalysis, 2004, vol. 346, # 4, p. 446 - 450]
[6]Olah, George A.; Husain, Altaf; Singh, Brij P.; Mehrotra, Ashok K. [Journal of Organic Chemistry, 1983, vol. 48, # 21, p. 3667 - 3672]
[7]Olah, George A.; Husain, Altaf; Singh, Brij P.; Mehrotra, Ashok K. [Journal of Organic Chemistry, 1983, vol. 48, # 21, p. 3667 - 3672]
[8]Ukaji, Yutaka; Koumoto, Naosuke; Fujisawa, Tamotsu [Chemistry Letters, 1989, p. 1623 - 1626]
[9]Bailey, Aaron D.; Baru, Ashvin R.; Tasche, Kendall K.; Mohan, Ram S. [Tetrahedron Letters, 2008, vol. 49, # 4, p. 691 - 694]
[10]Hanna, Ramsey D.; Naro, Yuta; Deiters, Alexander; Floreancig, Paul E. [Journal of the American Chemical Society, 2016, vol. 138, # 40, p. 13353 - 13360]
[11]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION - WO2018/26656, 2018, A1

18
[ 2235-01-0 ]
[ 7477-73-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	With trimethylsilylazide for 12h; Ambient temperature;

Reference： [1]Kirchmeyer, Stephan; Mertens, Alfred; Olah, George A. [Synthesis, 1983, # 6, p. 500 - 502]

19
[ 2235-01-0 ]
[ 762-72-1 ]
[ 81194-48-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With boron trifluoride In dichloromethane at 0℃; for 0.25h;

Reference： [1]Cella, J. A. [Journal of Organic Chemistry, 1982, vol. 47, # 11, p. 2125 - 2130]

20
[ 119-61-9 ]
[ 149-73-5 ]
[ 2235-01-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With Montmorillonite K 10; toluene-4-sulfonic acid In methanol at 20℃; for 48h;
98%	With cerium triflate In methanol at 20℃; for 5h;
98%	With triethylamine In methanol at 20℃; for 3h;	5. General procedure for the synthesis of dimethyl acetals catalyzed by ATRT General procedure: ATRT (99 mg, 1 mol%) was added to a mixture of undecanal (1a) (1.70 g, 10 mmol) and methyl orthoformate (2.12 g, 20 mmol) in dry MeOH (40 mL). The mixture was stirred at room temperature for 20 min. The mixture was filtered and the precipitate was washed with methanol. One drop of Et3N was added to the filterate and the solution was evaporated under reduced pressure. The residue was purified by column chromatography with hexane-acetone (20 : 1) containing one drop of Et3N on silica gelto give acetal 1c (2.07 g, 96%).

97%	With bismuth(lll) trifluoromethanesulfonate In methanol for 24h; Heating;
97%	With methanol at 50℃; for 6h;
93%	With hydrogenchloride In methanol for 4h; Heating;
92.61%	In methanol for 9h; Reflux;	10 Preparation of Dimethoxy diphenylmethane. Formula-(IIa3) Example-10 Preparation of Dimethoxy diphenylmethane. Formula-(IIa3) In a round bottom flask, (10 g) Benzophenone in 20 ml methanol was taken. 12 ml (2 equiv.) trimethyl orthoformate was added into the reaction mixture in a single lot and the reaction mixture was stirred at 25-30° C. 3-4 drop perchloric acid (HClO4 as a catalyst) was added and reflux it for 9 hr. After completion of the reaction, the reaction mass was dumped into water. Subsequently, the reaction mass was stirred for 15 min, filtered it and wash the solid mass with water to obtain white solid product. Weight: 11.6 g (92.61%) HPLC purity=92.68% ESI MS=196.8 [M-OMe]+ (-ve mode) M.P.=110-112° C. 1H NMR (400 MHZ) CDCl3: 7.5-7.4 (m, 4H), 7.3-7.26 (m, 4H), 7.22-7.18 (m, 2H), 3.12 (s, 6H). 13C NMR (400 MHz) (CDCl3): 142.5, 128.1, 127.5, 127.0, 102.9, 49.42
91%	In tetrachloromethane
82%	With toluene-4-sulfonic acid In methanol for 5h; Reflux;
78%	With toluene-4-sulfonic acid In methanol at 20℃; for 16h;
72%	With lithium tetrafluoroborate In ethanol for 24h; Heating;
	In methanol
	With toluene-4-sulfonic acid In methanol Heating;
	In methanol at 25 - 30℃; for 9h; Reflux;	10 Example-10: Preparation of Dimethoxy diphenylmethane. Formula- (Ha3)In a round bottom flask, (lOg) Benzophenone in 20 ml methanol was taken. 12 ml (2 equiv.) tri methyl orthoformate was added into the reaction mixture in a single lot and the reaction mixture was stirred at 25-30 °C. 3-4 drop perchloric acid (HCIO4 as a catalyst) was added and reflux it for 9 hr. After completion of the reaction, the reaction mass was dumped into water. Subsequently, the reaction mass was stirred for 15 min, filtered it and wash the solid mass with water to obtain white solid product.Weight: 11.6 g (92.61%)HPLC purity = 92.68 %ESI MS = 196.8 [M-OMe] + (-ve mode)M.P. = 1 10-112 °C NMR (400 MHz) CDC13: 7.5-7.4 (m, 4H), 7.3-7.26(m, 4H), 7.22-7.18 (m, 2H), 3.12 (s, 6H)13 C NMR (400 MHz) (CDCI3): 142.5, 128.1, 127.5, 127.0, 102.9, 49.42
	With toluene-4-sulfonic acid In methanol at 20 - 65℃; for 3h;	3 Benzhydrylidene-5- (bromo-pyrimidine-2-yl) -amine In a suitable flask with distillation bridge, 200 g Benzophenone (1,1 mol, 1.2 eq.) was added to1860 g Methanol (2350 ml) under stirring. To the reaction mixture, p-Toluene sulfonic acid monohydrate (4 g, 21 mmol) was added at room temperature under stirring. The mixture was heated to reflux temperature (65°C). Within 2 hours Trimethylorthoformate (175 g, 1,65 mol) was added under stirring while a mixture of Methanol and Methylformate was distilled off.About 190 to 210 g of distillate was collected at head temperature 58°C. After the addition was complete, the mixture was stirred for another 60 mm. Subsequently, the temperature was slowly raised to 100°C and further distillate (3040 g) was collected while 1,4-dioxane (3200 g, 3100 ml) was added in parallel. The reaction mixture is cooled to 80°C and 160 g (0.92 mol) 2-amino-5- bromo-pyrimidine was added under stirring. After addition of the 2-amino-5-bromo-pyrimidine,the reaction mixture is heated to 100°C and a mixture of Methanol and 1,4-dioxane was distilled off. The filling level of the reaction flask is continuously checked and if necessary, 1,4-Dioxane added to keep the filling level constant. After completion of the reaction (after approximately 16 hours, the conversion remained static), further 1,4-Dioxane is distilled (a net amount of 1440 g of solvent is removed from the mixture) and the batch is cooled while a suspension is formed. At approx. 60°C, MTBE (480 g, 650 ml) is added and the slurry is slowly cooled to roomtemperature (20-25°C). The solid was filtered and the residue washed with 80g of MTBE. Afterdrying at 40°C and 200 mbar over night in a tray drier, 246,9 g (80%) of the crude product with a purity of 98-99% was obtained. ‘H-NNR (400 MHz, dmso-d6)&r7.15-7.73 (m, bR), 8.73 (s, 2H) MP: 162-165°CMS (El+): M/Z = 337 Visual: white to beige solid.
	With toluene-4-sulfonic acid In methanol at 65℃; for 3h;	3; 4 In a suitable flask with distillation bridge, 200 g Benzophenone (1.1 mol, 1.2 eq.) was added to 1860 g Methanol (2350 ml) under stirring. To the reaction mixture, p-Toluene sulfonic acid monohydrate (4 g, 21 mmol) was added at room temperature under stirring. The mixture was heated to reflux temperature (65° C.). Within 2 hours Trimethylorthoformate (175 g, 1.65 mol) was added under stirring while a mixture of Methanol and Methylformate was distilled off. About 190 to 210 g of distillate was collected at head temperature 58° C. After the addition was complete, the mixture was stirred for another 60 min. Subsequently, the temperature was slowly raised to 100° C. and further distillate (3040 g) was collected while 1,4-dioxane (3200 g, 3100 ml) was added in parallel. The reaction mixture is cooled to 80° C. and 160 g (0.92 mol) 2-amino-5-bromo-pyrimidine was added under stirring. After addition of the 2-amino-5-bromo-pyrimidine, the reaction mixture is heated to 100° C. and a mixture of Methanol and 1,4-dioxane was distilled off. The filling level of the reaction flask is continuously checked and if necessary, 1,4-Dioxane added to keep the filling level constant. After completion of the reaction (after approximately 16 hours, the conversion remained static), further 1,4-Dioxane is distilled (a net amount of 1440 g of solvent is removed from the mixture) and the batch is cooled while a suspension is formed. At approx. 60° C., MTBE (480 g, 650 ml) is added and the slurry is slowly cooled to room temperature (20-25° C.). The solid was filtered and the residue washed with 80 g of MTBE. After drying at 40° C. and 200 mbar over night in a tray drier, 246.9 g (80%) of the crude product with a purity of 98-99% was obtained. 1H-NNR (400 MHz, dmso-d6) δ=7.15-7.73 (m, 10H), 8.73 (s, 2H) MP: 162-165° C. MS (E1+): M/Z=337
	With toluene-4-sulfonic acid In methanol; toluene Reflux; Large scale;	A.1 Step 1- Preparation of 3-bromo-N-(diphenylmethylene)-Benzenamine (compound 4) Step 1- Preparation of 3-bromo-N-(diphenylmethylene)-Benzenamine (compound 4) by reaction with benzophenone dimethyl ketal prepared "in situ" from benzophenone and trimethylorthoformate. Formation of the ketal: [0052] 100 kg of Benzophenone (550 Moles) are converted to the respective dimethyl ketal by treatment with 1.5 mole equivalents of trimethylorthoformate in a refluxing mixture of toluene and methanol (1:3, 5 L/kg benzophenone) under acid catalysis (5 mol% p-toluene sulfonic acid monohydrate). When the reaction is complete, solvents and access reagent are removed by distillation and replaced by toluene. To the resulting mixture, 1 mole equivalent of bromoaniline is added. The mixture is refluxed and partly concentrated until the conversion is complete (12 to 18 hours). Formed solids are removed by filtration and subsequently distillation is continued until the major part of the volatiles is removed. To the resulting concentrated solution/melt an equal amount of methanol is added and product crystallization is initiated by cooling. The resulting suspension is stirred for 30 min at 10 °C and subsequently the formed solid is collected by filtration. The solid is washed with methanol (0.5 L/kg benzophenone) and dried under vacuum to a constant weight at 25 °C. 158 kg of compound 4 are obtained (470 moles; 86% molar yield on benzophenone).
	With sulfuric acid In methanol at 25℃; for 24h; Inert atmosphere;

Reference： [1]Mansilla, Horacio; Regas, David [Synthetic Communications, 2006, vol. 36, # 15, p. 2195 - 2201]
[2]Location in patent: experimental part Ono, Fumiaki; Inatomi, Yoshiko; Tada, Yuusuke; Mori, Masaki; Sato, Tsuneo [Chemistry Letters, 2009, vol. 38, # 1, p. 96 - 97]
[3]Tanemura, Kiyoshi; Suzuki, Tsuneo [Chemistry Letters, 2015, vol. 44, # 6, p. 797 - 799]
[4]Leonard, Nicholas M.; Oswald, Matthew C.; Freiberg, Derek A.; Nattier, Bryce A.; Smith, Russell C.; Mohan, Ram S. [Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5202 - 5207]
[5]Gregg, Brian T.; Golden, Kathryn C.; Quinn, John F. [Tetrahedron, 2008, vol. 64, # 15, p. 3287 - 3295]
[6]Seebach, Dieter; Beck, Albert K.; Dahinden, Robert; Hoffmann, Matthias; Kuehnle, Florian N. M. [Croatica Chemica Acta, 1996, vol. 69, # 2, p. 459 - 484]
[7]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - US2012/202988, 2012, A1 Location in patent: Page/Page column 13
[8]Olah, George A.; Narang, Subhash C.; Meidar, David; Salem, George F. [Synthesis, 1981, # 4, p. 282 - 283]
[9]Franchini, Silvia; Sorbi, Claudia; Linciano, Pasquale; Carnevale, Gianluca; Tait, Annalisa; Ronsisvalle, Simone; Buccioni, Michela; Del Bello, Fabio; Cilia, Antonio; Pirona, Lorenza; Denora, Nunzio; Iacobazzi, Rosa Maria; Brasili, Livio [European Journal of Medicinal Chemistry, 2019, vol. 176, p. 310 - 325]
[10]Aepkers, Marion; Wuensch, Bernhard [Archiv der Pharmazie, 2004, vol. 337, # 2, p. 67 - 75]
[11]Hamada, Nao; Kazahaya, Kiyoshi; Shimizu, Hisashi; Sato, Tsuneo [Synlett, 2004, # 6, p. 1074 - 1076]
[12]Taylor,E.C.; Chiang,C.-S. [Synthesis, 1977, p. 467]
[13]Altava, Belen; Burguete; Garcia-Verdugo, Eduardo; Luis, Santiago V.; Miravet, Juan F.; Vicent, Maria J. [Tetrahedron Asymmetry, 2000, vol. 11, # 24, p. 4885 - 4893]
[14]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - WO2011/51960, 2011, A2 Location in patent: Page/Page column 25-26
[15]Current Patent Assignee: ROCHE HOLDING AG - WO2014/180752, 2014, A1 Location in patent: Page/Page column 39; 47; 48
[16]Current Patent Assignee: ROCHE HOLDING AG - US2014/330008, 2014, A1 Location in patent: Paragraph 0300-0306
[17]Current Patent Assignee: AMRI ITALY - EP2801577, 2014, A1 Location in patent: Paragraph 0051-0052
[18]Li, Jiawen; Qian, Bo; Huang, Hanmin [Organic Letters, 2018, vol. 20, # 22, p. 7090 - 7094]

21
[ 2235-01-0 ]
[ 141206-91-9 ]
[ 144402-27-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With toluene-4-sulfonic acid In dichloromethane for 3.5h; Ambient temperature;

Reference： [1]Mori, Yuji; Asai, Motoya; Okumura, Akiko; Furukawa, Hiroshi [Tetrahedron, 1995, vol. 51, # 18, p. 5299 - 5314]

22
[ 2235-01-0 ]
2-(tert-butyldimethylsilyl)oxy-10-<(tert-butyldimethylsilyl)oxy>methyl-8,9-dihydroxy-7-methyl-7,8,9,10-tetrahydrophenanthridine [ No CAS ]
(7R,7aS,10aR,11R)-11-Hydroxymethyl-7-methyl-9,9-diphenyl-7,7a,10a,11-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In dichloromethane at 40℃; for 2h;

Reference： [1]Shair, Matthew D.; Yoon, Tae Young; Mosny, Karoline K.; Chou; Danishefsky, Samuel J. [Journal of the American Chemical Society, 1996, vol. 118, # 40, p. 9509 - 9525]

23
[ 2235-01-0 ]
[ 1026935-14-7 ]
[ 181207-95-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With toluene-4-sulfonic acid In chloroform for 1.5h; Heating;

Reference： [1]Mori, Yuji; Yaegashi, Keisuke; Furukawa, Hiroshi [Tetrahedron, 1997, vol. 53, # 38, p. 12917 - 12932]

24
[ 2235-01-0 ]
[ 3886-69-9 ]
[ 59320-63-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 4 A molecular sieve; scandium tris(trifluoromethanesulfonate) In xylene for 16h; Heating;

Reference： [1]Heaney, Harry; Simcox, Michael T.; Slawin, Alexandra M.Z.; Giles, Robert G. [Synlett, 1998, # 6, p. 640 - 642]

25
[ 2235-01-0 ]
[ 193829-28-6 ]
2,2-Diphenyl-3-vinyl-tetrahydro-furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -20℃; for 0.333333h;

Reference： [1]Sano, Tomohumi; Oriyama, Takeshi [Synlett, 1997, vol. 1997, # 6, p. 716 - 718]

26
[ 2235-01-0 ]
[ 75-31-0 ]
[ 27126-12-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With 4 A molecular sieve; scandium tris(trifluoromethanesulfonate) In toluene for 16h; Heating;

Reference： [1]Heaney, Harry; Simcox, Michael T.; Slawin, Alexandra M.Z.; Giles, Robert G. [Synlett, 1998, # 6, p. 640 - 642]

27
[ 2235-01-0 ]
[ 100-46-9 ]
[ 7699-79-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 4 A molecular sieve; scandium tris(trifluoromethanesulfonate) In toluene for 16h; Heating;

Reference： [1]Heaney, Harry; Simcox, Michael T.; Slawin, Alexandra M.Z.; Giles, Robert G. [Synlett, 1998, # 6, p. 640 - 642]

28
[ 2235-01-0 ]
[ 97-30-3 ]
[ 220835-88-1 ]
[ 220835-89-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 40% 2: 40%	With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 60℃; for 9h;

Reference： [1]Di Donna, Leonardo; Napoli, Anna; Siciliano, Carlo; Sindona, Giovanni [Tetrahedron Letters, 1999, vol. 40, # 5, p. 1013 - 1014]

29
[ 93-56-1 ]
[ 2235-01-0 ]
2,2-diphenyl-4-phenyl-1,3-dioxolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With toluene-4-sulfonic acid In toluene for 1h; Heating;

Reference： [1]Einhorn, Cathy; Einhorn, Jacques; Marcadal-Abbadi, Celine; Pierre, Jean-Louis [Journal of Organic Chemistry, 1999, vol. 64, # 12, p. 4542 - 4546]

30
[ 2235-01-0 ]
[ 4360-65-0 ]

Yield	Reaction Conditions	Operation in experiment
	at 180℃;

Reference： [1]Blicke; Anderson [Journal of the American Chemical Society, 1952, vol. 74, p. 1733,1735]

31
[ 67-56-1 ]
[ 908093-98-1 ]
[ 2235-01-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 1h; var. alcohols, thiols and phenols;

Reference： [1]Oshima, Takumi; Nishioka, Ryoji; Nagai, Toshikazu [Tetrahedron Letters, 1980, vol. 21, p. 3919 - 3922]

32
[ 2235-01-0 ]
[ 154006-52-7 ]
(S)-2,2-Diphenyl-[1,3]dioxane-4-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With toluene-4-sulfonic acid In benzene

Reference： [1]Ohmori, Ken; Hachisu, Yoshifumi; Suzuki, Takao; Suzuki, Keisuke [Tetrahedron Letters, 2002, vol. 43, # 6, p. 1031 - 1034]

33
[ 3068-00-6 ]
[ 2235-01-0 ]
[ 717123-42-7 ]
2,2-diphenyl-1,3-dioxepan-5-ol [ No CAS ]
[ 717123-43-8 ]

Reference： [1]Archiv der Pharmazie,2004,vol. 337,p. 67 - 75

34
[ 3068-00-6 ]
[ 2235-01-0 ]
[ 717123-42-7 ]
[ 717123-43-8 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 6015 - 6028
[2]Archiv der Pharmazie,2004,vol. 337,p. 67 - 75

35
[ 2235-01-0 ]
1-ethoxycarbonylpiperidine-cis-3,4-diol [ No CAS ]
cis-2,2-diphenyl-tetrahydro[1,3]dioxolo[4,5-c]pyridine-5(4H)-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With toluene-4-sulfonic acid In toluene for 18h; Heating;

Reference： [1]Piergentili, Alessandro; Gentili, Francesco; Ghelfi, Francesca; Marucci, Gabriella; Pigini, Maria; Quaglia, Wilma; Giannella, Mario [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 18, p. 3901 - 3911]

36
[ 2235-01-0 ]
[ 59787-61-0 ]
C₇₅H₁₁₉N₁₁O₁₃ [ No CAS ]

Reference： [1]Chimia,2004,vol. 58,p. 237 - 240

37
[ 872104-51-3 ]
[ 2235-01-0 ]
(+)-(4R)-4-(2-azidoethyl)-2,2-diphenyl-1,3-dioxolan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With toluene-4-sulfonic acid; sodium sulfate In tetrahydrofuran for 3.5h; Heating;

Reference： [1]Aepkers, Marion; Wuensch, Bernhard [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6836 - 6849]

38
[ 872104-76-2 ]
[ 2235-01-0 ]
(-)-(4S)-4-azidomethyl-2,2-diphenyl-1,3-dioxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With toluene-4-sulfonic acid; sodium sulfate In tetrahydrofuran for 7h; Heating;

Reference： [1]Aepkers, Marion; Wuensch, Bernhard [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6836 - 6849]

39
[ 2235-01-0 ]
[ 661462-06-2 ]
(-)-(4S)-4-(2-azidoethyl)-2,2-diphenyl-1,3-dioxolan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With toluene-4-sulfonic acid; sodium sulfate In tetrahydrofuran for 3.5h; Heating;

Reference： [1]Aepkers, Marion; Wuensch, Bernhard [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6836 - 6849]

40
[ 2235-01-0 ]
[ 872104-77-3 ]
(+)-(4R)-4-azidomethyl-2,2-diphenyl-1,3-dioxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With toluene-4-sulfonic acid; sodium sulfate In tetrahydrofuran for 7h; Heating;

Reference： [1]Aepkers, Marion; Wuensch, Bernhard [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6836 - 6849]

41
[ 69-65-8 ]
[ 2235-01-0 ]
[ 898568-52-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	With tin(ll) chloride In 1,2-dimethoxyethane for 14h; Heating;
56%	With tin(ll) chloride In 1,2-dimethoxyethane for 14h; Reflux;
	With tin(ll) chloride In 1,2-dimethoxyethane for 16h; Inert atmosphere; Reflux;

Reference： [1]Sydorenko, Nadiya; Hsung, Richard P.; Vera, Eymi L. [Organic Letters, 2006, vol. 8, # 12, p. 2611 - 2614]
[2]Location in patent: experimental part Banerjee, Ashutosh; Schepmann, Dirk; Köhler, Jens; Würthwein, Ernst-Ulrich; Wünsch, Bernhard [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 22, p. 7855 - 7867]
[3]MacDonald, Melissa J.; Schipper, Derek J.; Ng, Peter J.; Moran, Joseph; Beauchemin, Andre M. [Journal of the American Chemical Society, 2011, vol. 133, # 50, p. 20100 - 20103]

42
Acetic acid (3S,4S,5R,6R)-3,4-dihydroxy-1,7-dioxa-spiro[5.5]undec-5-yl ester [ No CAS ]
[ 2235-01-0 ]
C₂₄H₂₆O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With sulfuric acid In dichloromethane for 24h; Heating;

Reference： [1]Ghosh, Sunil K.; Ko, Changhong; Liu, Jia; Wang, Jiashi; Hsung, Richard P. [Tetrahedron, 2006, vol. 62, # 45, p. 10485 - 10496]

43
[ 2235-01-0 ]
[ 166516-67-2 ]
[ 904690-67-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 22 - 50℃; for 8h;

Reference： [1]Pozsgay, Vince; Ekborg, Goeran; Sampathkumar, Srinivasa-Gopalan [Carbohydrate Research, 2006, vol. 341, # 10, p. 1408 - 1427]

44
[ 608-68-4 ]
[ 2235-01-0 ]
2,2-diphenyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In benzene at 80℃; Heating / reflux;	1.B To a 50 mL round-bottomed flask equipped with a distillation apparatus was added ^-dimethyl tartrate (0.5 g, 2.8 mmol, 1 equiv), dimethoxydiphenylmethane (0.66 g, 3.1 mmol, 1.1 equiv) and a catalytic amount of /7-TsOH following by 15 mL of anhydrous benzene. The resulting mixture was refluxed until the azeotrope benzene-water was removed (~80°C). After cooling the mixture to room temperature, the solution was diluted in EtOAc and the organic layer was washed with a saturated NaHCθ3 solution (1 x 15 mL), water (1 x 15 mL), and brine (1 x 15 mL). The organic layer was dried over MgSO4, filtered, and evaporated in vacuo to afford a brown oil. The resulting oil is then purified via flash chromatography (90:10, hexane:EtOAc) to afford diphenyl acetal tartrate (0.578 g, 1.60 mmol, 60 %) as a white solid which was spectroscopically identical to a previously reported compound (B. Altava et al, Tetrahedron: Asymmetry, 2000, 11: 4885-4893: J. Irrure et al, Tetrahedron: Asymmetry, 1992, 3: 1591-1596). A solution 0.72 g of 2,2- diphenyl-[l,3]dioxolane-4,5-dicarboxylic acid dimethyl ester (2.0 mmol, 1 equiv) in THF (10 mL) was added dropwise to solution of (phenanthren-9-yl)magnesium bromide (10 mmol, 5 equiv) prepared from 2.7 g of 9-bromophenanthrene and 0.25 g of Mg powder and catalytic amount of iodine) in THF (40 mL) at room temperature. The reaction mixture was then stirred at room temperature for 12 hours. The reaction was quenched by careful addition of a saturated solution of NH4Cl. The organic layer was separated and the aqueous layer extracted twice with ether (2 x 50 mL). After the combined organic layers were dried using MgSO-), the solvent was removed in vacuo to afford a yellow oil. Purification via flash chromatography (80:20 hexanes/EtOAc) afforded a white solid which was then submitted to recrystallization using benzene/hexanes (1/1 ca, 40 mL). After drying under high vacuum for 5 hours, 1.48 g (1.5 mmol, 75 %) of 7e was isolated as a white solid.[0150] Compound 7e. White solid: mp 314-3170C; [α]D21 = +519° (c = 1.3, CHCl3); BR. vmax (flm): 3548, 3060, 1497, 1450, 1223, 1103, 896 cm"1; 1H NMR (400 MHz, DMSO-d6> 421 K) δ 8.70-8.20 (6 H, m), 7.80 (1 H, s), 7.70-7.50 (6 H3 m), 7.30-7.10 (4 H, m), 7.0-6.70 (6 H, m) ppm; 13C (100 MHz, DMSO-d6> 421 K) δ 143.9, 139.8, 138. 2, 131.9, 131.8, 131.7, 131.6, 131.3, 131.0, 130.9, 129.8, 129.6, 129.4, 129.0, 128.9, 128.3, 128, 127.9, 127.85 127.5, 127.3, 126.4, 126.1, 126.0, 125.9, 125.6, 125.5, 123.6, 123.4, 123.3, 123.1, 111.3, 84.9, 81.8 ppm; HRMS (APPI+) m/z calculated for C73H50O4 991.1757 found 1013.3808 (M+Na).

Reference： [1]Current Patent Assignee: BOSTON UNIVERSITY - WO2007/139749, 2007, A2 Location in patent: Page/Page column 41-42

45
[ 881734-00-5 ]
[ 2235-01-0 ]
[ 934271-83-7 ]

Yield	Reaction Conditions	Operation in experiment
48.9%	With toluene-4-sulfonic acid In toluene for 13h; Heating;

Reference： [1]Dei, Silvia; Bellucci, Cristina; Buccioni, Michela; Ferraroni, Marta; Guandalini, Luca; Manetti, Dina; Martini, Elisabatta; Marucci, Gabriella; Matucci, Rosanna; Nesi, Marta; Romanelli, Maria Novella; Scapecchi, Serena; Teodori, Elisabetta [Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1409 - 1413]

46
[ 2235-01-0 ]
[ 934271-84-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 48.9 percent / p-TsOH*H₂O / toluene / 13 h / Heating 2: 86.6 percent / LiAlH₄ / diethyl ether / 4 h / -18 - 20 °C

Reference： [1]Dei, Silvia; Bellucci, Cristina; Buccioni, Michela; Ferraroni, Marta; Guandalini, Luca; Manetti, Dina; Martini, Elisabatta; Marucci, Gabriella; Matucci, Rosanna; Nesi, Marta; Romanelli, Maria Novella; Scapecchi, Serena; Teodori, Elisabetta [Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1409 - 1413]

47
[ 2235-01-0 ]
[ 934271-85-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: p-TsOH*H₂O / toluene / 13 h / Heating 2: LiAlH₄ / diethyl ether / 4 h / -18 - 20 °C

Reference： [1]Dei, Silvia; Bellucci, Cristina; Buccioni, Michela; Ferraroni, Marta; Guandalini, Luca; Manetti, Dina; Martini, Elisabatta; Marucci, Gabriella; Matucci, Rosanna; Nesi, Marta; Romanelli, Maria Novella; Scapecchi, Serena; Teodori, Elisabetta [Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1409 - 1413]

48
[ 2235-01-0 ]
C₂₁H₂₆NOS⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 48.9 percent / p-TsOH*H₂O / toluene / 13 h / Heating 2: 86.6 percent / LiAlH₄ / diethyl ether / 4 h / -18 - 20 °C 3: diethyl ether / 20 °C

Reference： [1]Dei, Silvia; Bellucci, Cristina; Buccioni, Michela; Ferraroni, Marta; Guandalini, Luca; Manetti, Dina; Martini, Elisabatta; Marucci, Gabriella; Matucci, Rosanna; Nesi, Marta; Romanelli, Maria Novella; Scapecchi, Serena; Teodori, Elisabetta [Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1409 - 1413]

49
[ 2235-01-0 ]
C₂₁H₂₆NOS⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: p-TsOH*H₂O / toluene / 13 h / Heating 2: LiAlH₄ / diethyl ether / 4 h / -18 - 20 °C 3: diethyl ether / 20 °C

Reference： [1]Dei, Silvia; Bellucci, Cristina; Buccioni, Michela; Ferraroni, Marta; Guandalini, Luca; Manetti, Dina; Martini, Elisabatta; Marucci, Gabriella; Matucci, Rosanna; Nesi, Marta; Romanelli, Maria Novella; Scapecchi, Serena; Teodori, Elisabetta [Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1409 - 1413]

50
[ 2235-01-0 ]
(R,R)-2,2-diphenyl-α,α,α'α'-tetraphenanthren-9-yl-1,3-dioxolane-4,5-dimethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 60 percent / p-TsOH / benzene / 80 °C 2: 75 percent / tetrahydrofuran / 12 h / 20 °C

Reference： [1]Gerard, Baudouin; Sangji, Sheharbano; O'Leary, Daniel J.; Porco Jr., John A. [Journal of the American Chemical Society, 2006, vol. 128, # 24, p. 7754 - 7755]

51
[ 2235-01-0 ]
2-((R)-2,2-Diphenyl-[1,3]dioxolan-4-yl)-ethylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 59 percent / Na₂SO₄; p-toluenesulfonic acid / tetrahydrofuran / 3.5 h / Heating 2: 100 percent / H₂ / Pd/C / tetrahydrofuran / 1.5 h / 20 °C / 750.06 Torr

Reference： [1]Aepkers, Marion; Wuensch, Bernhard [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6836 - 6849]

52
[ 2235-01-0 ]
2-((S)-2,2-Diphenyl-[1,3]dioxolan-4-yl)-ethylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 54 percent / Na₂SO₄; p-toluenesulfonic acid / tetrahydrofuran / 3.5 h / Heating 2: 97 percent / H₂ / Pd/C / tetrahydrofuran / 1.5 h / 20 °C / 750.06 Torr

Reference： [1]Aepkers, Marion; Wuensch, Bernhard [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6836 - 6849]

53
[ 2235-01-0 ]
<i>C</i>-(2,2-diphenyl-[1,3]dioxan-4-yl)-methylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 67 percent / Na₂SO₄; p-toluenesulfonic acid / tetrahydrofuran / 7 h / Heating 2: 96 percent / H₂ / Pd/C / tetrahydrofuran / 1.5 h / 20 °C / 750.06 Torr

Reference： [1]Aepkers, Marion; Wuensch, Bernhard [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6836 - 6849]

54
[ 2235-01-0 ]
<i>C</i>-(2,2-diphenyl-[1,3]dioxan-4-yl)-methylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 71 percent / Na₂SO₄; p-toluenesulfonic acid / tetrahydrofuran / 7 h / Heating 2: 100 percent / H₂ / Pd/C / tetrahydrofuran / 1.5 h / 20 °C / 750.06 Torr

Reference： [1]Aepkers, Marion; Wuensch, Bernhard [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6836 - 6849]

55
[ 2235-01-0 ]
2-(2,2-diphenyl-1,3-dioxolan-4-yl)ethan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 41 percent Spectr_. / pTsOH*H₂O / tetrahydrofuran / 240 h / 20 °C 2: 96 percent / Et₃N / CH₂Cl₂ / 48 h / 4 °C 3: 87 percent / NaN₃ / dimethylformamide / 2.5 h / Heating 4: 88 percent / H₂ / 10 percent Pd/C / tetrahydrofuran / 1.5 h / 20 °C / 750.06 Torr

Reference： [1]Aepkers, Marion; Wuensch, Bernhard [Archiv der Pharmazie, 2004, vol. 337, # 2, p. 67 - 75]

56
[ 2235-01-0 ]
1-(2,2-diphenyl-1,3-dioxan-4-yl)methanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 59 percent Spectr_. / pTsOH*H₂O / tetrahydrofuran / 240 h / 20 °C 2: 74 percent / Et₃N / CH₂Cl₂ / 48 h / 4 °C 3: 91 percent / NaN₃ / dimethylformamide / 9 h / Heating 4: 98 percent / H₂ / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 750.06 Torr

Reference： [1]Aepkers, Marion; Wuensch, Bernhard [Archiv der Pharmazie, 2004, vol. 337, # 2, p. 67 - 75]

57
[ 2235-01-0 ]
[ 124918-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: p-toluenesulfonic acid / propan-2-ol / 0.17 h / Heating 2: H₂ / 10percent Pd/C / methanol

Reference： [1]Thurkauf; Mattson; Richardson; Mirsadeghi; Ornstein; Harrison Jr.; Rice; Jacobson; Monn [Journal of Medicinal Chemistry, 1992, vol. 35, # 8, p. 1323 - 1329]

58
[ 2235-01-0 ]
[ 139132-85-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: p-toluenesulfonic acid / propan-2-ol / 0.17 h / Heating 2: H₂ / 10percent Pd/C / methanol 3: 88 percent / Et₃N / CHCl₃ / 0.17 h

Reference： [1]Thurkauf; Mattson; Richardson; Mirsadeghi; Ornstein; Harrison Jr.; Rice; Jacobson; Monn [Journal of Medicinal Chemistry, 1992, vol. 35, # 8, p. 1323 - 1329]

59
[ 2235-01-0 ]
[ 139132-74-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: p-toluenesulfonic acid / propan-2-ol / 0.17 h / Heating 2: H₂ / 10percent Pd/C / methanol 3: 88 percent / Et₃N / CHCl₃ / 0.17 h 4: NH₃ / methanol; H₂O / 2 h

Reference： [1]Thurkauf; Mattson; Richardson; Mirsadeghi; Ornstein; Harrison Jr.; Rice; Jacobson; Monn [Journal of Medicinal Chemistry, 1992, vol. 35, # 8, p. 1323 - 1329]

60
[ 2235-01-0 ]
[ 139132-75-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: p-toluenesulfonic acid / propan-2-ol / 0.17 h / Heating 2: H₂ / 10percent Pd/C / methanol 3: 88 percent / Et₃N / CHCl₃ / 0.17 h 4: methanol; H₂O / 2 h

Reference： [1]Thurkauf; Mattson; Richardson; Mirsadeghi; Ornstein; Harrison Jr.; Rice; Jacobson; Monn [Journal of Medicinal Chemistry, 1992, vol. 35, # 8, p. 1323 - 1329]

61
[ 2235-01-0 ]
[ 6317-10-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 100 percent / H₂O / Nafion-H / acetone / 0.5 h 2: 100 percent / Nafion-H / benzene / Heating

Reference： [1]Olah, George A.; Narang, Subhash C.; Meidar, David; Salem, George F. [Synthesis, 1981, # 4, p. 282 - 283]

62
[ 2235-01-0 ]
[ 84543-37-3 ]
C₂₁H₂₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	In tetrahydrofuran at 20℃;	Preparation of Ketone YT-41 Preparation of ketone YT-41 To a solution of benzophenone (4.86 g, 30 mmol) and trimethyl orthoformate (3.1 mL, 30 mmol) in methanol (20 mL) was added TsOH.H2O (0.02 g). After the solution was heated at 50-60 C. for 3 hours (during this time methyl formate formed was distilled off), the bath temperature was raised to 100 C. to distill off the methanol. Upon cooling to room temperature, a solution of alcohol YT-31 (6.18 g, 30 mmol) in THF (150 mL) was added, followed by 3 drops of 70% perchloric acid. After being stirred at room temperature overnight, the reaction mixture was neutralized with con. NH4OH and concentrated. The resulting residue was dissolved in dichloromethane (150 mL), washed with brine, dried over sodium sulfate, concentrated, and purified by flash chromatography (hexane:ether, 10:1 to 5:2, v/v) to give alcohol YT-40 as a solid (7.24 g, 67%). 1H NMR: d7.55-7.20 (m, 10H), 4.37-3.54 (m, 10H), 3.43 (dd, J=7.1, 7.1 Hz, 1H), 2.37 (d, J=7.4 Hz, 1H). 13C NMR: d143.3, 142.7, 128.3, 128.2, 126,3, 126,2, 126.1, 109.6, 96.02, 77.42, 74.10, 71.01, 69.08, 65.68, 60.44, 59.78. PCC (4.0 g, 18.6 mmol) was added portionwise over 15 min to a mixture of alcohol YT-40 (2.79 g, 8.1 mmol) and powdered 3A molecular sieves (80 g) in dichloromethane (80 mL). After being stirred for 3 hours under nitrogen, the reaction mixture was filtered through celite and washed carefully with ether. The filtrate was concentrated and purified by passing through a short silica gel column (hexane:ether, 1:1, v/v) to afford YT-41 as a white solid (1.43 g, 51%). 1H NMR: d7.6-7.2 (m, 10H), 4.79 (d, J=6.6 Hz, 1H), 4.53 (dd, J=6.4, 1.8 Hz, 1H), 4.32 (d, J=13.4, 1H), 4.18 (dd, J=13.4, 2.4 Hz, 1H), 4.07 (dt, J=11.2, 3.2 Hz, 1H), 3.85 (d, J=12.4 Hz, 1H), 3.80-3.57 (m, 4H); 13C NMR: d197.8, 141.9, 140.9, 128.8, 128.5, 128.4, 128.2, 126.5, 110.8, 94.17, 78.58, 75.63, 67.47, 65.60, 60.44, 59.55. Anal. Calcd. for C21H20O6: C, 68.47; H, 5.47. Found: C, 68.34; H, 5.85.

Reference： [1]Current Patent Assignee: COLORADO STATE UNIVERSITY SYSTEM - US6348608, 2002, B1 Location in patent: Page column 71

63
[ 119-61-9 ]
[ 149-73-5 ]
[ 107-31-3 ]
[ 2235-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In methanol at 50 - 100℃; for 3h;	Preparation of Ketone YT-41 Preparation of ketone YT-41 To a solution of benzophenone (4.86 g, 30 mmol) and trimethyl orthoformate (3.1 mL, 30 mmol) in methanol (20 mL) was added TsOH.H2O (0.02 g). After the solution was heated at 50-60 C. for 3 hours (during this time methyl formate formed was distilled off), the bath temperature was raised to 100 C. to distill off the methanol. Upon cooling to room temperature, a solution of alcohol YT-31 (6.18 g, 30 mmol) in THF (150 mL) was added, followed by 3 drops of 70% perchloric acid. After being stirred at room temperature overnight, the reaction mixture was neutralized with con. NH4OH and concentrated. The resulting residue was dissolved in dichloromethane (150 mL), washed with brine, dried over sodium sulfate, concentrated, and purified by flash chromatography (hexane:ether, 10:1 to 5:2, v/v) to give alcohol YT-40 as a solid (7.24 g, 67%). 1H NMR: d7.55-7.20 (m, 10H), 4.37-3.54 (m, 10H), 3.43 (dd, J=7.1, 7.1 Hz, 1H), 2.37 (d, J=7.4 Hz, 1H). 13C NMR: d143.3, 142.7, 128.3, 128.2, 126,3, 126,2, 126.1, 109.6, 96.02, 77.42, 74.10, 71.01, 69.08, 65.68, 60.44, 59.78. PCC (4.0 g, 18.6 mmol) was added portionwise over 15 min to a mixture of alcohol YT-40 (2.79 g, 8.1 mmol) and powdered 3A molecular sieves (80 g) in dichloromethane (80 mL). After being stirred for 3 hours under nitrogen, the reaction mixture was filtered through celite and washed carefully with ether. The filtrate was concentrated and purified by passing through a short silica gel column (hexane:ether, 1:1, v/v) to afford YT-41 as a white solid (1.43 g, 51%). 1H NMR: d7.6-7.2 (m, 10H), 4.79 (d, J=6.6 Hz, 1H), 4.53 (dd, J=6.4, 1.8 Hz, 1H), 4.32 (d, J=13.4, 1H), 4.18 (dd, J=13.4, 2.4 Hz, 1H), 4.07 (dt, J=11.2, 3.2 Hz, 1H), 3.85 (d, J=12.4 Hz, 1H), 3.80-3.57 (m, 4H); 13C NMR: d197.8, 141.9, 140.9, 128.8, 128.5, 128.4, 128.2, 126.5, 110.8, 94.17, 78.58, 75.63, 67.47, 65.60, 60.44, 59.55. Anal. Calcd. for C21H20O6: C, 68.47; H, 5.47. Found: C, 68.34; H, 5.85.

Reference： [1]Current Patent Assignee: COLORADO STATE UNIVERSITY SYSTEM - US6348608, 2002, B1 Location in patent: Page column 71

64
[ 96-27-5 ]
[ 2235-01-0 ]
[ 186603-59-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,3-benzoxazine-2,4-dione In benzene	9.A A. A. 2,2-Diphenyl-5-hydroxymethyl-1,3-oxathiolane (1) 3-Mercapto-1,2-propanediol(3.26 g, 30.00 mmol) was dissolved in benzene (60 mL). Benzophenone dimethyl ketal (13.48 g, 60.0 mmol, 2 equiv.) and CSA (0.70 mg, 3.00 mmol, 0.1 equiv.) were added. The solution was heated with an oil bath to reflux. Benzene/methanol was collected and removed while more benzene was added to the refluxing reaction. After about 200 mL benzene/methanol was distilled out, the reaction was cooled to room temperature, applied directly onto a silica gel column. The column was then eluted was 20%-40% ether/petroleum ether to afford a thick oil as the desired product (3.78 g, 46). Rf =0.25, 20% ether/petroleum ether. 1 H NMR (400 MHz, C6 D6) δ=2.56 (dd, J=6.3, 10.2 Hz, 1H), 2.83 (dd, J=7.7, 10.2 Hz, 1H), 3.35 (br dd, J=5.3, 11.6 Hz, 1H), 3.44 (br dd, J=3.5, 11.6 Hz, 1H), 3.88-3.95 (m, 1H), 6.94-7.20 (m, 6H), 7.54 (d, J=7.5 Hz, 2H), 7.70 (d, J=7.5 Hz, 2H). 13 C NMR (100 MHz, C6 D6) δ=35.90, 63.97, 83.29, 100.20, 126-129 (m).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US5831004, 1998, A

65
[ 2235-01-0 ]
phenyl 1-thio-α-L-rhamnopyranose [ No CAS ]
[ 148777-96-2 ]

Yield	Reaction Conditions	Operation in experiment
39%	With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 50℃; for 8h;

Reference： [1]Location in patent: experimental part Crich, David; Li, Ming [Journal of Organic Chemistry, 2008, vol. 73, # 18, p. 7003 - 7010]

66
[ 2235-01-0 ]
[ 14917-55-6 ]
[ 148777-95-1 ]

Yield	Reaction Conditions	Operation in experiment
47%	With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 50℃; for 8h;
	With camphor-10-sulfonic acid In acetonitrile

Reference： [1]Location in patent: experimental part Crich, David; Li, Ming [Journal of Organic Chemistry, 2008, vol. 73, # 18, p. 7003 - 7010]
[2]Location in patent: scheme or table Szikra, Dezso; Mándi, Attila; Borbás, Anikó; Nagy, István P.; Komáromi, István; Kiss-Szikszai, Attila; Herczeg, Mihály; Antus, Sándor [Carbohydrate Research, 2011, vol. 346, # 13, p. 2004 - 2006]

67
[ 42890-76-6 ]
[ 2235-01-0 ]
[ 1115323-17-5 ]
(S)-2-(2,2-diphenyl-1,3-dioxan-4-yl)methanol [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 6015 - 6028

68
[ 4328-94-3 ]
[ 2235-01-0 ]
[ 1115322-98-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With toluene-4-sulfonic acid; sodium sulfate In tetrahydrofuran for 7h; Reflux; Inert atmosphere;
73%	With toluene-4-sulfonic acid In tetrahydrofuran for 12h; Reflux;	5.1.10. 2-(2,2-Diphenyl-1,3-dioxan-4-yl)ethan-1-ol (16) Benzophenone dimethyl acetal (14, 913 mg, 4.0 mmol) was added to a solution of pentane-1,3,5-triol (8, 340 mg, 2.8 mmol) and p-toluenesulfonic acid (86.1 mg, 0.5 mmol) in THF (10 mL). The mixture was heated to reflux for 12 h. The solvent was removed in vacuo, the residue was dissolved in Et2O and the solution was extracted with a saturated solution of NaHCO3 (5 mL). The Et2O layer was dried (MgSO4), concentrated in vacuo and the residue was purified by fc (4 cm, petroleum ether:EtOAc = 60:40, 10 mL, Rf = 0.36). Colorless solid, mp 61 °C, yield 332 mg (73%). C18H20O3 (284.4). Anal. calcd. C 76.03, H 7.10; found C 75.89, H 7.00. MS (EI): m/z (%) = 284 [M, 2], 239 [M-CH2CH2OH, 2], 207 [M-Ph, 100], 105 [PhCO+,64]. IR (ATR, neat): inlMMLBox (cm-1) = 3294 (OH), 2954, 2934, 2874 (C-H), 1096, 1025 (C-O), 768, 746 (ArC-H). 1H NMR (CDCl3): δ (ppm) = 1.39 (dq, J = 12.8/2.3 Hz, 1H, 5-Heq), 1.76-1.85 (m, 1H 5-Hax), 1.88-2.01 (m, 2H, CH2-CH2-OH), 2.14 (dd, J = 6.1/4.7 Hz, 1H, CH2-CH2-OH), 3.90-3.96 (m, 2H, CH2-CH2-OH), 4.04 (dt, J = 11.6/2.5 Hz, 1H, 6-Hax), 4.08 (td, J = 11.6/2.1 Hz, 1H, 6-Heq), 4.12-4.20 (m, 1H, 4-Hax), 7.17-7.30 (m, 4H, Harom), 7.36-7.48 (m, 4H, Harom), 7.53-7.54 (m, 2H, Harom).

Reference： [1]Location in patent: experimental part Sax, Michael; Froehlich, Roland; Schepmann, Dirk; Wuensch, Bernhard [European Journal of Organic Chemistry, 2008, # 35, p. 6015 - 6028]
[2]Location in patent: experimental part Utech, Tina; Köhler, Jens; Wünsch, Bernhard [European Journal of Medicinal Chemistry, 2011, vol. 46, # 6, p. 2157 - 2169]

69
[ 2235-01-0 ]
[ 71998-70-4 ]
[ 1115323-56-2 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 6015 - 6028

70
[ 13171-64-7 ]
[ 2235-01-0 ]
2,2-diphenyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester [ No CAS ]

Reference： [1]Organic Letters,2010,vol. 12,p. 880 - 882

71
[ 2235-01-0 ]
[ 1263104-42-2 ]
[ 1263104-49-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With camphor-10-sulfonic acid In acetonitrile for 3h; Reflux;

Reference： [1]Location in patent: experimental part Etayo, Pablo; Badorrey, Ramon; Diaz-De-Villegas, Maria D.; Galvez, Jose A. [Advanced Synthesis and Catalysis, 2010, vol. 352, # 18, p. 3329 - 3338]

72
[ 2235-01-0 ]
C₂₅H₁₉Cl₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / toluene / 25 - 30 °C / Reflux 1.2: 3 h / Reflux 2.1: triethylamine / dichloromethane / 3 h / 0 - 10 °C
	Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / toluene / Reflux 1.2: 3 h / Reflux 2.1: triethylamine / dichloromethane / 3 h / 0 - 5 °C

Reference： [1]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - WO2011/51960, 2011, A2
[2]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - US2012/202988, 2012, A1

73
[ 2235-01-0 ]
[ 1296664-70-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / toluene / 25 - 30 °C / Reflux 1.2: 3 h / Reflux 2.1: triethylamine / dichloromethane / 3 h / 0 - 10 °C 3.1: dmap / toluene / 0 - 30 °C
	Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / toluene / 25 - 30 °C / Reflux 1.2: 3 h / Reflux 2.1: triethylamine / dichloromethane / 3 h / 0 - 30 °C 3.1: dmap / toluene / 0.08 h / 0 - 10 °C 3.2: 7 h / 25 - 30 °C

Reference： [1]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - WO2011/51960, 2011, A2
[2]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - WO2011/51960, 2011, A2

74
[ 2235-01-0 ]
[ 1296664-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / toluene / 25 - 30 °C / Reflux 1.2: 3 h / Reflux 2.1: triethylamine / dichloromethane / 3 h / 0 - 30 °C
	Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / toluene / Reflux 1.2: 3 h / Reflux 2.1: triethylamine / dichloromethane / 3 h / 25 - 30 °C

Reference： [1]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - WO2011/51960, 2011, A2
[2]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - US2012/202988, 2012, A1

75
[ 4767-03-7 ]
[ 2235-01-0 ]
[ 1296664-69-1 ]

Yield	Reaction Conditions	Operation in experiment
69.4%	Stage #1: 2,2-bis(hydroxymethyl)propionic acid In toluene Reflux; Stage #2: dimethoxydiphenylmethane In toluene for 3h; Reflux;	11 Preparation of 5-methyl-2,2-diphenyl-1,3-dioxane-5-carboxylic acid. Formula-(IIb3) Example-11 Preparation of 5-methyl-2,2-diphenyl-1,3-dioxane-5-carboxylic acid. Formula-(IIb3) In a round bottom flask, (12 g) 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoic acid and 35 ml toluene was taken. (99.4 mg) p-toluene sulfonic acid was added into the reaction mixture at 25-30° C. temperature. The reaction mixture was heated at reflux temperature, and 20.5 g (1 equiv.) dimethoxy diphenylmethane [IIa3] in 35 ml toluene was added and it was further refluxed under dean stark. Continuous removal and addition of toluene done upto 3 hrs. Then reaction mixture was cooled at 25-30° C. and dumped into water. The reaction mixture was stirred at 20-30° C. and filter it and wash the solid mass with water to obtain white solid product. Weight: 18.16 gm (69.4% Yield) M.P.=195-197° C. HPLC purity=94.5%. After Acid-Base to obtained 99.6% purity. 1H NMR (400 MHZ) CDCl3: 7.52-7.5 (m, 2H), 7.45-7.32 (m, 2H), 7.39-7.35 (m, 2H), 7.31-7.3 (m, 1H), 7.29-7.28 (m, 2H), 7.26-7.22 (m, 1H), 4.32-4.29 (d, J=11.6 Hz, 2H), 3.78-3.75 (d, J=11.6 Hz, 2H), 1.19 (s, 3H).
	Stage #1: 2,2-bis(hydroxymethyl)propionic acid In toluene at 25 - 30℃; Reflux; Stage #2: dimethoxydiphenylmethane In toluene for 3h; Reflux;	11 Example- 1 1: Preparation of 5-methyl-2,2-diphenyl-l,3-dioxane-5-carboxylic acid. Formula- (Hb3)In a round bottom flask, (12g) 3-hydroxy-2-(hydroxymethyl)-2- methylpropanoic acid and 35 ml toluene was taken. (99.4mg) p-toluene sulfonic acid was added into the reaction mixture at 25-30 °C temperature. The reaction mixture was heated at reflux temperature, and 20.5 g (1 equiv.) dimethoxy diphenylmethane [IIa3] in 35 ml toluene was added and it was further refluxed under dean stark. Continuous removal and addition of toluene done upto 3 hrs. Then reaction mixture was cooled at 25-30 °C and dumped into water. The reaction mixture was stirred at 20-30 °C and filter it and wash the solid mass with water to obtain white solid product.Weight: 18.16 gm (69.4% Yield)M.P. = 195-197°CESI MS =298.9[M+], 336.9ΓΜ+ ] + (+ve mode)= 296.8[M-l] + (-ve mode)HPLC purity = 94.5%.After Acid-Base to obtained 99.6% purity.lH NMR (400 MHz) CDC13: 7.52-7.5( m,2H), 7.45-7.32(m ,2H) , 7.39-7.35(m,2H),7.31-7.3(m,lH), 7.29-7.28(m,2H), 7.26-7.22(m,lH), 4.32-4.29(d, J=11.6Hz,2H), 3.78-3.75(d, J=l 1.6Hz, 2H), 1.19(s,3H)I.R. (in KBr) = 3059 cm'1, 1707.66 cm"1

Reference： [1]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - US2012/202988, 2012, A1 Location in patent: Page/Page column 13
[2]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - WO2011/51960, 2011, A2 Location in patent: Page/Page column 26

76
[ 2235-01-0 ]
C₆₉H₉₅NO₁₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / toluene / Reflux 1.2: 3 h / Reflux 2.1: triethylamine / dichloromethane / 3 h / 0 - 5 °C 3.1: dmap / 19.5 h / 0 - 30 °C
	Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / toluene / Reflux 1.2: 3 h / Reflux 2.1: triethylamine / dichloromethane / 3 h / 25 - 30 °C 3.1: dmap / toluene / 0.08 h 3.2: 7 h / 25 - 30 °C

Reference： [1]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - US2012/202988, 2012, A1
[2]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - US2012/202988, 2012, A1

77
[ 2235-01-0 ]
[ 117994-55-5 ]
[ 4741-41-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With toluene-4-sulfonic acid In isopropyl alcohol for 1h; Reflux;	4.2.6.5 (+)-Dexoxadrol 1 General procedure: To a refluxing solution of 12 (0.14g, 1mmol) in IPA with PTSA (cat), was added dimethoxybenzophenone (1.61g, 7mmol) and refluxed further for 1h. The reaction mixture was cooled, concentrated and as such subjected to column purification to give pure 1 (SiO2, hexane/EtOAc, 7:3) (0.18g, 60%). To compound 1 (0.31g, 1mmol) in EtOAc (5mL), passed dry HCl gas liberated from the reaction of concd H2SO4 over NaCl. The reaction mixture was concentrated to dryness to give pure 1·HCl (0.27g, 80%).

Reference： [1]Bhat, Chinmay; Tilve, Santosh G. [Tetrahedron, 2013, vol. 69, # 51, p. 10876 - 10883]

78
[ 2235-01-0 ]
(R)-(S)-1-Piperidin-2-yl-ethane-1,2-diol [ No CAS ]
[ 117178-67-3 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In isopropyl alcohol for 1h; Reflux;	General procedure: To a refluxing solution of 12 (0.14g, 1mmol) in IPA with PTSA (cat), was added dimethoxybenzophenone (1.61g, 7mmol) and refluxed further for 1h. The reaction mixture was cooled, concentrated and as such subjected to column purification to give pure 1 (SiO2, hexane/EtOAc, 7:3) (0.18g, 60%). To compound 1 (0.31g, 1mmol) in EtOAc (5mL), passed dry HCl gas liberated from the reaction of concd H2SO4 over NaCl. The reaction mixture was concentrated to dryness to give pure 1·HCl (0.27g, 80%).

Reference： [1]Bhat, Chinmay; Tilve, Santosh G. [Tetrahedron, 2013, vol. 69, # 51, p. 10876 - 10883]

79
[ 13735-81-4 ]
[ 2235-01-0 ]
[ 1626437-11-3 ]

Yield	Reaction Conditions	Operation in experiment
35%	With solid acid of tin(IV) ion-exchanged montmorillonite In dichloromethane at 0℃; for 5h; Inert atmosphere;	General reaction procedure of the Mukaiyama aldol reactions General procedure: A ketone (1.0 mmol) was added to a CH2Cl2 (2 mL) suspension of Sn-Mont (40 mg) which had been activated in a vacuum at 120 °C for 1 h, and then silicon enolate (2.0 mmol) was added. The mixture was stirred at 0 °C under a nitrogen atmosphere. After the reaction was completed, the catalyst was filtered off and washed with cold CH2Cl2. The yields of products were determined by 1H NMR analysis of the filtrate using mesitylene as the internal standard. The assignment of relative configuration (threo or erythro) of the aldol products 3ac, 3bc, and 3dc was made with 13C NMR analysis based on the upfield chemical shifts of the methine carbon in the erythro isomer compared with those in the threo isomer.5 The silylated aldol products were purified by silica-gel column chromatography eluting with hexane/AcOEt = 10-40 : 1.

Reference： [1]Takehira, Satoshi; Masui, Yoichi; Onaka, Makoto [Chemistry Letters, 2014, vol. 43, # 4, p. 498 - 500]

80
[ 7752-82-1 ]
[ 2235-01-0 ]
[ 1072850-89-5 ]

Yield	Reaction Conditions	Operation in experiment
246.9 g	In 1,4-dioxane at 80 - 100℃; for 16h;	3 Benzhydrylidene-5-(bromopyrimidine-2-yl)amine In a suitable flask with distillation bridge, 200 g Benzophenone (1,1 mol, 1.2 eq.) was added to1860 g Methanol (2350 ml) under stirring. To the reaction mixture, p-Toluene sulfonic acid monohydrate (4 g, 21 mmol) was added at room temperature under stirring. The mixture was heated to reflux temperature (65°C). Within 2 hours Trimethylorthoformate (175 g, 1,65 mol) was added under stirring while a mixture of Methanol and Methylformate was distilled off.About 190 to 210 g of distillate was collected at head temperature 58°C. After the addition was complete, the mixture was stirred for another 60 min. Subsequently, the temperature was slowly raised to 100°C and further distillate (3040 g) was collected while 1,4-dioxane (3200 g, 3100 ml) was added in parallel. The reaction mixture is cooled to 80°C and 160 g (0.92 mol) 2-amino-5- bromo-pyrimidine was added under stirring. After addition of the 2-amino-5-bromopyrimidine,the reaction mixture is heated to 100°C and a mixture of Methanol and 1,4-dioxane was distilled off. The filling level of the reaction flask is continuously checked and if necessary, 1,4-dioxane added to keep the filling level constant. After completion of the reaction (after approximately 16 hours, the conversion remained static), further 1,4-Dioxane is distilled (a net amount of 1440 g of solvent is removed from the mixture) and the batch is cooled while a suspension is formed. At approx. 60°C, MTBE (480 g, 650 ml) is added and the slurry is slowly cooled to roomtemperature (20-25°C). The solid was filtered and the residue washed with 80g of MTBE. After drying at 40°C and 200 mbar over night in a tray drier, 246,9 g (80%) of the crude product with a purity of 98-99% was obtained. 1H-NMR (400 MHz, dmso-d6) δ= 7.15-7.73 (m, bR), 8.73 (s, 2H) MP: 162-165°C MS (El+): M/Z = 337 Visual: white to beige solid.
	With toluene-4-sulfonic acid In 1,4-dioxane at 114 - 120℃; Inert atmosphere;	3; 4 Example 3 Benzhydrylidene-5-(bromo-pyrimidine-2-yl)-amine In a suitable flask with distillation bridge, 200 g Benzophenone (1.1 mol, 1.2 eq.) was added to 1860 g Methanol (2350 ml) under stirring. To the reaction mixture, p-Toluene sulfonic acid monohydrate (4 g, 21 mmol) was added at room temperature under stirring. The mixture was heated to reflux temperature (65° C.). Within 2 hours Trimethylorthoformate (175 g, 1.65 mol) was added under stirring while a mixture of Methanol and Methylformate was distilled off. About 190 to 210 g of distillate was collected at head temperature 58° C. After the addition was complete, the mixture was stirred for another 60 min. Subsequently, the temperature was slowly raised to 100° C. and further distillate (3040 g) was collected while 1,4-dioxane (3200 g, 3100 ml) was added in parallel. The reaction mixture is cooled to 80° C. and 160 g (0.92 mol) 2-amino-5-bromo-pyrimidine was added under stirring. After addition of the 2-amino-5-bromo-pyrimidine, the reaction mixture is heated to 100° C. and a mixture of Methanol and 1,4-dioxane was distilled off. The filling level of the reaction flask is continuously checked and if necessary, 1,4-Dioxane added to keep the filling level constant. After completion of the reaction (after approximately 16 hours, the conversion remained static), further 1,4-Dioxane is distilled (a net amount of 1440 g of solvent is removed from the mixture) and the batch is cooled while a suspension is formed. At approx. 60° C., MTBE (480 g, 650 ml) is added and the slurry is slowly cooled to room temperature (20-25° C.). The solid was filtered and the residue washed with 80 g of MTBE. After drying at 40° C. and 200 mbar over night in a tray drier, 246.9 g (80%) of the crude product with a purity of 98-99% was obtained. [0302] 1H-NNR (400 MHz, dmso-d6) [0303] δ=7.15-7.73 (m, 10H), 8.73 (s, 2H) [0304] MP: 162-165° C. [0305] MS (E1+): M/Z=337 [0306] Visual: white to beige solid.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2014/180752, 2014, A1 Location in patent: Page/Page column 47; 48
[2]Current Patent Assignee: ROCHE HOLDING AG - US2014/330008, 2014, A1 Location in patent: Paragraph 0300-0306

81
[ 2235-01-0 ]
[ 591-19-5 ]
[ 1020180-02-2 ]

Yield	Reaction Conditions	Operation in experiment
158 kg	In toluene Reflux; Large scale;	A.1 Step 1- Preparation of 3-bromo-N-(diphenylmethylene)-Benzenamine (compound 4) Step 1- Preparation of 3-bromo-N-(diphenylmethylene)-Benzenamine (compound 4) by reaction with benzophenone dimethyl ketal prepared "in situ" from benzophenone and trimethylorthoformate. Formation of the ketal: [0052] 100 kg of Benzophenone (550 Moles) are converted to the respective dimethyl ketal by treatment with 1.5 mole equivalents of trimethylorthoformate in a refluxing mixture of toluene and methanol (1:3, 5 L/kg benzophenone) under acid catalysis (5 mol% p-toluene sulfonic acid monohydrate). When the reaction is complete, solvents and access reagent are removed by distillation and replaced by toluene. To the resulting mixture, 1 mole equivalent of bromoaniline is added. The mixture is refluxed and partly concentrated until the conversion is complete (12 to 18 hours). Formed solids are removed by filtration and subsequently distillation is continued until the major part of the volatiles is removed. To the resulting concentrated solution/melt an equal amount of methanol is added and product crystallization is initiated by cooling. The resulting suspension is stirred for 30 min at 10 °C and subsequently the formed solid is collected by filtration. The solid is washed with methanol (0.5 L/kg benzophenone) and dried under vacuum to a constant weight at 25 °C. 158 kg of compound 4 are obtained (470 moles; 86% molar yield on benzophenone).

Reference： [1]Current Patent Assignee: AMRI ITALY - EP2801577, 2014, A1 Location in patent: Paragraph 0051-0052; 0056

82
[ 2235-01-0 ]
[ 117994-55-5 ]
(+)-dexoxadrol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With toluene-4-sulfonic acid In isopropyl alcohol Reflux;

Reference： [1]Bhat, Chinmay [ChemistryOpen, 2015, vol. 4, # 2, p. 192 - 196]

83
[ 2235-01-0 ]
(R)-(S)-1-Piperidin-2-yl-ethane-1,2-diol [ No CAS ]
(-)-epidexoxadrol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With toluene-4-sulfonic acid In isopropyl alcohol Reflux;

Reference： [1]Bhat, Chinmay [ChemistryOpen, 2015, vol. 4, # 2, p. 192 - 196]

84
[ 2235-01-0 ]
[ 20224-38-8 ]
2,2-diphenyl-3a,4,7,7a-tetrahydro-4,7-methanobenzo[d][1,3]dioxole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With toluene-4-sulfonic acid In dichloromethane at 25℃; for 18h; Inert atmosphere;

Reference： [1]Maier, Lukáš; Khirsariya, Prashant; Hylse, Ondřej; Adla, Santosh Kumar; Černová, Lenka; Poljak, Michal; Krajčovičová, Soňa; Weis, Erik; Drápela, Stanislav; Souček, Karel; Paruch, Kamil [Journal of Organic Chemistry, 2017, vol. 82, # 7, p. 3382 - 3402]

85
[ 2235-01-0 ]
[ 200499-58-7 ]
(R)-1-benzyloxycarbonyl-2-[(S)-2,2-diphenyl-1,3-dioxolan-4-yl]pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With tin(ll) chloride In 1,2-dimethoxyethane for 3h; Reflux;	(R)-1-Benzyloxycarbonyl-2-[(S)-2,2-diphenyl-1,3-dioxolan-4-yl]pyrrolidine (6) SnCl2 (8.7 mg, 0.046 mmol) was added to a solution of compound 5(242 mg, 0.91 mmol) and diphenyldimethoxymethane (416 mg,1.82 mmol) in DME (7 mL) and the resulting mixture was stirred andheated under reflux conditions for 3 h. The reaction was quenched with pyridine(8 L) and concentrated in vacuo. Purification of the residue by silica gel columnchromatography (first eluent: Et2O/hexanes, 1:4; second eluent Et2O/hexanes, 1:1)yielded 355 mg (91% yield) of compound 6 as a pale yellow oil.

Reference： [1]Castán, Alejandro; Badorrey, Ramón; Gálvez; Díaz-De-Villegas [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 612 - 619]

86
[ 2235-01-0 ]
[ 200499-65-6 ]
C₂₇H₂₇NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tin(ll) chloride In 1,2-dimethoxyethane Reflux;	General procedure for the synthesis of organocatalysts OC4-OC10 General procedure: SnCl2 (9.5 mg, 0.05 mmol) was added to a solution of compound 7 (265 mg,1.00 mmol) and the corresponding dimethoxyacetal (2 mmol) in DME (7 mL) and the resulting mixture was stirred and heated under reflux until complete disappearance of7 (monitored by TLC). The reaction was quenched with pyridine (8 L), concentratedin vacuo and the residue was purified by silica gel column chromatography (firsteluent: Et2O/hexanes, 1:4; second eluent Et2O/hexanes, 1:1). The resultingcompound was dissolved in EtOH (18 mL per mmol of substrate) and hydrogenatedwith molecular hydrogen for 12 h at atmospheric pressure and room temperature inthe presence of 10% Pd/C (8 mg per 100 mg of substrate) as a catalyst. The catalystwas removed by filtration through a Celite pad and the solvent was evaporated invacuo. CH2Cl2 (20 mL) and 2 M aqueous NaOH (10 mL) were added. The aqueouslayer was separated and extracted with CH2Cl2 (2 × 10 mL). The combined organicextracts were dried over anhydrous MgSO4, filtered and concentrated in vacuo.Purification of the residue by silica gel column chromatography (eluent: EtOAc/EtOH,1:1 1% v/v Et3N) yielded the corresponding organocatalysts OC4-OC10.

Reference： [1]Castán, Alejandro; Badorrey, Ramón; Gálvez; Díaz-De-Villegas [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 612 - 619]

87
[ 2235-01-0 ]
C₁₄H₂₂O₃ [ No CAS ]
C₂₇H₃₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With toluene-4-sulfonic acid In toluene at 20℃; for 8h; Inert atmosphere;

Reference： [1]Wu, Zhiyong; Lebœuf, David; Retailleau, Pascal; Gandon, Vincent; Marinetti, Angela; Voituriez, Arnaud [Chemical Communications, 2017, vol. 53, # 52, p. 7026 - 7029]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	2235-01-0	MDL No. :	MFCD00025900
Formula :	C₁₅H₁₆O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NYRVXYOKUZSUDA-UHFFFAOYSA-N
M.W :	228.29	Pubchem ID :	75228
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 2235-01-0 ] {[proInfo.proName]}

Quality Control of [ 2235-01-0 ]

Related Doc. of [ 2235-01-0 ]

Product Details of [ 2235-01-0 ]

Safety of [ 2235-01-0 ]

Application In Synthesis of [ 2235-01-0 ]

[ 2235-01-0 ] Synthesis Path-Downstream 1~87

Related Functional Groups of
[ 2235-01-0 ]

Aryls

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 2235-01-0 ] {[proInfo.proName]}

Quality Control of [ 2235-01-0 ]

Related Doc. of [ 2235-01-0 ]

Product Details of [ 2235-01-0 ]

Safety of [ 2235-01-0 ]

Application In Synthesis of [ 2235-01-0 ]

[ 2235-01-0 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 2235-01-0 ]

Aryls

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2235-01-0 ]