Name: 588-53-4|4-(Benzylideneamino)phenol|98%
Brand: Ambeed
SKU: A250146
Price: 11.0 USD
Availability: InStock
Rating: 93 (22 reviews)

1
[ 74-96-4 ]
[ 588-53-4 ]
[ 15484-91-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; ethanol at 100℃;

Reference： [1]Current Patent Assignee: Hoechster Farbw. - DE69006, 1800, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 55][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 55]

2
[ 100-02-7 ]
[ 588-53-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; iron beim Erwaermen der mit Magnesiumoxid versetzten Reaktionsloesung mit Benzaldehyd;
	Multi-step reaction with 2 steps 1: platinum(IV) oxide; hydrogen / methanol / 1 h / 20 °C 2: methanol / 1 h / 20 °C

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - US2027902, 1933, A
[2]Sreedhar, Bojja; Rawat, Vikas S. [Synthetic Communications, 2012, vol. 42, # 17, p. 2490 - 2502]

3
[ 588-53-4 ]
[ 103-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; In methanol; at 20℃; for 1h;	General procedure: To a stirring solution of 4-aminophenol (2.18 g, 20 mmol) in 50 mL of methanol was added an aldehyde or ketone (20 mmol). The resulting solution was refluxed for 3 h. After cooling to room temperature sodium borohydride (908 mg, 24 mmol) was added portionwise. The reaction mixture was stirred for another 1 h and then poured into 50 mL of water. After extraction with CH2Cl2 (20 mL) three times, the combined organic phase was dried over Na2SO4, and the solvent was removed in vacuo to afford 4-alkylaminophenol as colorless or yellowish oil, or crystals in an almost quantitative yield. The crude product was used in the next step without further purification.18

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4817 - 4820
[2]Journal of the Chemical Society. Perkin transactions I,1985,p. 437 - 440
[3]Journal of Organic Chemistry,2018,vol. 83,p. 11886 - 11895
[4]Patent: US2394587,1942,
[5]Patent: US2063151,1934,
[6]Patent: US2063151,1934,
[7]Patent: DE211869,
[8]Zeitschrift fur Elektrochemie und angewandte physikalische Chemie,1912,vol. 18,p. 749
[9]Doklady Akademii Nauk SSSR,1937,vol. 14,p. 17,21
[10]Chemical and pharmaceutical bulletin,1971,vol. 19,p. 1722 - 1727
[11]ARKIVOC,2010,vol. 2010,p. 293 - 299
[12]Synthetic Communications,2012,vol. 42,p. 2490 - 2502
[13]Tetrahedron,2014,vol. 70,p. 4323 - 4330

4
[ 123-30-8 ]
[ 100-52-7 ]
[ 588-53-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	In ethanol for 1.5h; Heating / reflux;	1 EXAMPLE 1 EXAMPLE 1 [00027] [C00006] Ethanol (200 proof, 515 g) and p-aminophenol (300 g, 2.75 mol) were charged into a 2L 3-neck round bottom flask equipped with a thermometer and a condenser. Benzaldehyde (292 g, 2.75 mol) was added from an additional funnel while maintaining a slow and steady flow and while stirring. Another portion of ethanol (150 g) was added and the whole mixture was heated to reflux for 1.5 h. After cooling down to room temperature, the solid thus formed was collected by filtration and washed three times with ethanol (3×50 ml) and dried. 492 g (91%) of the imine product (structure above) was obtained as a pale yellow powder.
90%	In methanol for 2h; Inert atmosphere; Schlenk technique; Reflux;
88.9%	In methanol for 1h;

88%	With dodecatungstosilicic acid; phosphorous pentoxide In neat (no solvent, solid phase) at 20℃;
83%	In toluene for 16h; Reflux;
81%	In ethanol Microwave irradiation;	Synthesis of Schiffbases by Microwave method General procedure: A mixture of various aromatic aldehydes (4mmol) and para- aminophenol (4mmol) in ethanol (1mL) were added in sample mi- crowave tube. The contents were subjected to microwave irradia- tion at 100 W for about 4-8 min. Progress of the reaction was mon- itored by TLC. After the completion of the reaction, solid product was obtained in reaction mixture which was filtered and recrystal- lized with ethanol. Recrystallization provides the title compounds as solid crystals.
78%	In ethanol for 1h; Heating;
76.9%	In ethanol for 1.5h; Reflux;	3 Example 3 Preparation of 4-benzylidene aminophenol (IVa) 2.1 g (19.3 mmol) of 4-aminophenol was dissolved in 28 ml ethanol, and 1.9 ml (19.3 mmol) benzaldehyde was added. The mixture was heated to the reflux temperature and reacted for 1.5 h, Then, the reaction mixture was cooled to the room temperature and the solid separated out from the mixture was filtered by sucking. The filter cake was washed with a small amount of ethanol and dried to obtain 3 g of a yellow solid with the yield of 76.9%. m.p. 182-183° C.
72%	With piperidine In ethanol Heating;
64%	In ethanol for 2h; Reflux; Acidic conditions;
64%	In ethanol for 2h; Reflux;
	With acetic acid
	With acetic acid
	With ethanol
	With ethanol
	In diethyl ether
	In ethanol for 2h; Heating;
	With mesoporous silica for 0.133333h; Microwave irradiation;
	In methanol
	In methanol at 20℃; for 1h;
	With triethylamine In ethanol at 90℃; for 2h;
	In toluene Dean-Stark;
	With mesoporous silica In neat (no solvent) for 0.133333h; Microwave irradiation; Green chemistry;
	In methanol for 3h; Reflux;	4.2 General procedure for the synthesis of 4-alkylaminophenols via the reductive amination General procedure: To a stirring solution of 4-aminophenol (2.18 g, 20 mmol) in 50 mL of methanol was added an aldehyde or ketone (20 mmol). The resulting solution was refluxed for 3 h. After cooling to room temperature sodium borohydride (908 mg, 24 mmol) was added portionwise. The reaction mixture was stirred for another 1 h and then poured into 50 mL of water. After extraction with CH2Cl2 (20 mL) three times, the combined organic phase was dried over Na2SO4, and the solvent was removed in vacuo to afford 4-alkylaminophenol as colorless or yellowish oil, or crystals in an almost quantitative yield. The crude product was used in the next step without further purification.18
	In tetrahydrofuran Reflux; Inert atmosphere;
	In ethanol at 20℃; for 3.25h;
	With magnesium(II) sulfate In dichloromethane at 20℃; for 2h;
	In ethanol Reflux;
	In ethanol at 20℃; for 0.5h;
	With formic acid In ethanol for 3h; Reflux; Inert atmosphere;
	With sulfuric acid In ethanol for 2h; Resolution of racemate;	2.1. Synthesis of benzylideneanilines General procedure: Generally, the appropriate benzaldehyde (1 mmol) and aniline (0.1 mmol) derivatives were combined in anhydrous ethanol (5 mL), along with 1-2 drops of concentrated sulphuric acid and the mixture refluxed for 2 hours. The mother liquor was then stored at ca. 0 °C for ∼12 hrs. prior to vacuum filtration of the resulting precipitate. All compounds were recrystallized from ethanol prior to storage in a desiccator. Melting points for all compounds were also determined ( See S3 ).
	With magnesium(II) sulfate In tetrahydrofuran at 20℃; for 4.5h; Inert atmosphere;	Synthesis of Formula 17 Add 4-aminophenol (0.05 mol) and benzaldehyde (0.05 mol) to 200 ml of THF and stir for 30 minutes under a nitrogen stream.MgSO4(0.1 mol) was added and reacted for 4 hours while maintaining room temperature.After removing the solvent from the reaction product, extraction was performed using distilled water and MC to remove the solvent, and column separation was performed using an eluent of EAc/Hexane to synthesize 4-(benzylideneamino)phenol, a compound of Formula 17.
79.95 %Chromat.	With oxygen In acetonitrile at 30℃; for 18h;
	With trimethyl orthoformate Reflux;

Reference： [1]Current Patent Assignee: MILLIKEN & COMPANY - US6667392, 2003, B2 Location in patent: Page column 5
[2]Sowa, Sylwia; Pietrusiewicz, K. Michał [European Journal of Organic Chemistry, 2019, vol. 2019, # 5, p. 923 - 938]
[3]Location in patent: experimental part Wang, Renchao; Xu, Jiaxi [ARKIVOC, 2010, vol. 2010, # 9, p. 293 - 299]
[4]Fareed, Ghulam; Versiani, Muhammad Ali; Afza, Nighat; Fareed, Nazia; Kalhoro, Mahboob Ali; Yasmeen, Shazia; Anwar, Muhammad Aijaz [Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 2, p. 426 - 430]
[5]Location in patent: scheme or table da Silva, Cleiton M.; da Silva, Danielle L.; Martins, Cleide V.B.; de Resende, Maria A.; Dias, Esther S.; Magalhaes, Thais F.F.; Rodrigues, Leticia P.; Sabino, Adao A.; Alves, Rosemeire B.; de Fatima, Angelo [Chemical Biology and Drug Design, 2011, vol. 78, # 5, p. 810 - 815]
[6]Abdelakder, Hellal; Abdellah, Benhamou; Mohamed, Mersellem [Journal of Molecular Structure, 2021, vol. 1241]
[7]De, Rajib Lal; Mandal, Mahuya; Roy, Lovely; Mukherjee, Jaydeep [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2008, vol. 47, # 2, p. 207 - 213]
[8]Current Patent Assignee: BEIJING UNDERPROVED MEDICAL TECHNOLOGY - US2013/85140, 2013, A1 Location in patent: Paragraph 0043
[9]Odabasoglu, Mustafa; Turgut, Guenseli; Karaer, Hatice [Phosphorus, Sulfur and Silicon and the Related Elements, 1999, vol. 152, p. 9 - 25]
[10]Location in patent: experimental part Ashraf, Muhammad Aqeel; Wajid, Abdul; Mahmood, Karamat; Maah, Mohd. Jamil; Yusoff, Ismail [Oriental Journal of Chemistry, 2011, vol. 27, # 2, p. 363 - 372]
[11]Location in patent: experimental part Khosa, Muhammad Kaleem; Chatha, Shahzad Ali Shahid; Nisar, Madhia; Zia, Khalid Mahmood; Khalil-Ur-Rehman; Jamal, Muhammad Asghar; Yousaf, Muhammad [Journal of the Chemical Society of Pakistan, 2011, vol. 33, # 3, p. 421 - 425]
[12]Porai-Koschiz et al. [Zhurnal Obshchei Khimii, 1947, vol. 17, p. 1774,1781][Chem.Abstr., 1948, p. 5863]
[13]Pope [Journal of the Chemical Society, 1908, vol. 93, p. 537] Haegele [Chemische Berichte, 1892, vol. 25, p. 2753][Chemische Berichte, 1893, vol. 26, p. 394]
[14]Porai-Koschiz et al. [Zhurnal Obshchei Khimii, 1947, vol. 17, p. 1774,1781][Chem.Abstr., 1948, p. 5863]
[15]Philipp [Chemische Berichte, 1892, vol. 25, p. 3248]
[16]O'Connor, Charmian J.; Mitha, Amin S. H. [Australian Journal of Chemistry, 1986, vol. 39, # 2, p. 259 - 269]
[17]Isse, Abdirisak Ahmed; Abdurahman, Ahmed Maye; Vianello, Elio [Journal of the Chemical Society. Perkin Transactions 2 (2001), 1996, vol. 4, p. 597 - 600]
[18]Location in patent: experimental part Kumar, B. R. Prashantha; Masih, Pankaj; Lukose, Chris Raju; Abraham, Nimmy; Priya; Xavier, Rinu Mary; Saji, Kesiya; Adhikary, Laxmi [Journal of Heterocyclic Chemistry, 2009, vol. 46, # 2, p. 336 - 339]
[19]Makal, Anna; Schilf, Wojciech; Kamienski, Bohdan; Szady-Chelmieniecka, Anna; Grech, Eugeniusz; Wozniak, Krzysztof [Dalton Transactions, 2011, vol. 40, # 2, p. 421 - 430]
[20]Location in patent: experimental part Sreedhar, Bojja; Rawat, Vikas S. [Synthetic Communications, 2012, vol. 42, # 17, p. 2490 - 2502]
[21]Location in patent: experimental part Zhang, Ye; Zou, Biqun; Wang, Kai; Pan, Yingming; Liang, Hong; Yi, Xianghui; Wang, Hengshan [Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1341 - 1346]
[22]Fernandes, Sergio Antonio; Do Couto Tavares, Eder; Teixeira, Robson Ricardo; Da Silva, Cleiton Moreira; Montanari, Ricardo Marques; De Fatima, Angelo; Anconi, Cleber Paulo Andrada; De Almeida, Wagner Batista; Dos Santos, Helio Ferreira; Da Silva, Antonio Alberto [Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2013, vol. 75, # 1-2, p. 197 - 204]
[23]Sharma, Gyanendra Kumar; Sharma, Naveen Kumar; Pathak, Devender [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 2, p. 266 - 272]
[24]Abdellaoui, Hassane; Xu, Jiaxi [Tetrahedron, 2014, vol. 70, # 29, p. 4323 - 4330]
[25]Hirata, Goki; Yamada, Naoshi; Sanada, Shohei; Onodera, Gen; Kimura, Masanari [Organic Letters, 2015, vol. 17, # 3, p. 600 - 603]
[26]Cao, Chao-Tun; Zhou, Wei; Cao, Chenzhong [Journal of Physical Organic Chemistry, 2017, vol. 30, # 10]
[27]Xi, Zi-Wei; Yang, Lei; Wang, Dan-Yan; Pu, Chao-Dan; Shen, Yong-Miao; Wu, Chuan-De; Peng, Xiao-Gang [Journal of Organic Chemistry, 2018, vol. 83, # 19, p. 11886 - 11895]
[28]Cao, Chao-Tun; Cheng, Shimao; Zhang, Jingyuan; Cao, Chenzhong [Journal of Physical Organic Chemistry, 2019, vol. 32, # 3]
[29]Cao, Chao-Tun; Zhou, Wei; Cao, Chenzhong [Journal of Physical Organic Chemistry, 2020, vol. 33, # 3]
[30]Besli, Serap; Doğan, Semih; Mutlu Balci, Ceylan; Tümay, Süreyya Oğuz; Yeşi̇Lot, Serkan [Turkish Journal of Chemistry, 2020, vol. 44, # 1, p. 31 - 47]
[31]Robertson, Tahjna I.; Nelson, Peter N. [Journal of Molecular Structure, 2022, vol. 1249]
[32]Current Patent Assignee: DIC CORP.; AK HOLDINGS, INC. - KR101509448, 2015, B1 Location in patent: Paragraph 0237-0240
[33]Mal, Diptangshu Datta; Pradhan, Debabrata [Inorganic Chemistry, 2022, vol. 61, # 4, p. 2211 - 2218]
[34]Current Patent Assignee: CLEVELAND CLINIC - WO2022/47086, 2022, A1 Location in patent: Paragraph 0006; 0073

5
[ 588-53-4 ]
[ 74-88-4 ]
[ 783-08-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium carbonate In acetone for 96h; Inert atmosphere; Schlenk technique; Reflux;
	With methanol; potassium hydroxide

Reference： [1]Sowa, Sylwia; Pietrusiewicz, K. Michał [European Journal of Organic Chemistry, 2019, vol. 2019, # 5, p. 923 - 938]
[2]Philipp [Chemische Berichte, 1892, vol. 25, p. 3248]

6
[ 292638-84-7 ]
[ 588-53-4 ]
[ 5855-62-9 ]
[ 103-14-0 ]
[ 138409-88-8 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 1842 - 1848
[2]Journal of Organic Chemistry,1992,vol. 57,p. 1842 - 1848

7
[ 588-53-4 ]
[ 71105-17-4 ]
[ 75644-24-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	In acetonitrile for 4h;

Reference： [1]Griffiths, David; Hull, Roy; Seden, Timothy P. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1240 - 1244]

8
[ 588-53-4 ]
[ 58670-19-2 ]
[ 86380-86-1 ]

Yield	Reaction Conditions	Operation in experiment
45%	With triethylamine In chloroform Heating;

Reference： [1]Tewari, R. S.; Parihar, P. [Tetrahedron, 1983, vol. 39, # 1, p. 129 - 136]

9
[ 588-53-4 ]
[ 5855-62-9 ]
[ 103-14-0 ]
[ 138409-88-8 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 1842 - 1848

10
[ 588-53-4 ]
[ 108-24-7 ]
[ 81575-56-6 ]

Yield	Reaction Conditions	Operation in experiment
42.1%	With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In dichloromethane for 6h;

Reference： [1]Singh, Serjinder; Sharma, Vijay K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 12, p. 1087 - 1088]

11
[ 588-53-4 ]
[ 123-62-6 ]
4-benzylideneaminophenyl propionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In benzene for 2h;

Reference： [1]O'Connor, Charmian J.; Mitha, Amin S. H. [Australian Journal of Chemistry, 1986, vol. 39, # 2, p. 259 - 269]

12
[(Z)-4-Hydroxy-phenylimino]-phenyl-acetic acid [ No CAS ]
[ 588-53-4 ]

Yield	Reaction Conditions	Operation in experiment
99 % Chromat.	With tributylphosphine In tetrahydrofuran; pyridine at 25℃; for 2h;

Reference： [1]Barton, Derek H. R.; Taran, Frederic [Tetrahedron Letters, 1998, vol. 39, # 27, p. 4777 - 4780]

13
[ 623-73-4 ]
[ 588-53-4 ]
cis-ethyl 1-(o-hydroxyphenyl)-3-phenylaziridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With lanthanum(lll) triflate In ethanol at 20℃; for 12h;

Reference： [1]Xie, Wenhua; Fang, Jianwen; Li, Jun; Wang, Peng George [Tetrahedron, 1999, vol. 55, # 45, p. 12929 - 12938]

14
[ 588-53-4 ]
[ 4778-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dicobalt octacarbonyl; benzene at 230℃;

Reference： [1]Murahashi et al. [Nippon Kagaku Zasshi, 1958, vol. 79, p. 68,79][Chem.Abstr., 1960, p. 5558]

15
[ 588-53-4 ]
aqueous alcoholic sodium acetate [ No CAS ]
[ 103-14-0 ]

Reference： [1]Zeitschrift fur Elektrochemie und angewandte physikalische Chemie,1912,vol. 18,p. 749

16
[ 588-53-4 ]
C₇₈H₆₀N₉O₆P₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: 4-benzylidenamino-phenol With sodium hydride In tetrahydrofuran; mineral oil Inert atmosphere; Stage #2: With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In tetrahydrofuran; mineral oil for 48h; Inert atmosphere; Reflux;	2.3.2. General procedure used for synthesis of compounds 3a-3d Compound 2a (2.13 g; 10.8 mmol) was dissolved in 10 mL of dry THF in a 100 mL three-necked round-bottomed flask and NaH (60% oil suspension, 0.45 g; 10.8 mmol) in 5 mL of dry THF was quickly added dropwise to the stirred solution under an argon atmosphere. Then a solution of hexachlorocyclotriphosphazene (1) (0.40 g; 1.2 mmol) in 5 mL of THF was prepared and added by dropping funnel dropwise to the stirred solution of 2a. The reaction was stirred under reflux for 48 h. The reaction was followed by TLC on silica gel plates using n-hexane-THF (3:2) as the mobile phase. The reaction mixture was filtered to remove the sodium chloride and any other insoluble material. The excess THF was removed under reduced pressure and then the reaction mixture was extracted with DCM/distilled water phase for separation from excess Schiff base. n-Hexane was slowly added to the solution and the solids precipitated. The resulting solids were filtered, washed with n-hexane, and then dried at room temperature. Compound 3a was crystallized from the n-heptane-THF (2:1). A summary of the preparation of all compounds is given in Table 1.
65%	Stage #1: 4-benzylidenamino-phenol With sodium Stage #2: With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In tetrahydrofuran for 8h; Heating;

Reference： [1]Besli, Serap; Doğan, Semih; Mutlu Balci, Ceylan; Tümay, Süreyya Oğuz; Yeşi̇Lot, Serkan [Turkish Journal of Chemistry, 2020, vol. 44, # 1, p. 31 - 47]
[2]Odabasoglu, Mustafa; Turgut, Guenseli; Karaer, Hatice [Phosphorus, Sulfur and Silicon and the Related Elements, 1999, vol. 152, p. 9 - 25]

17
[ 588-53-4 ]
[ 7460-82-4 ]
C₃₀H₂₈N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In N,N-dimethyl-formamide

Reference： [1]Houjou, Hirohiko; Tsuzuki, Seiji; Nagawa, Yoshinobu; Hiratani, Kazuhisa [Bulletin of the Chemical Society of Japan, 2002, vol. 75, # 4, p. 831 - 839]

18
[ 589-57-1 ]
[ 588-53-4 ]
3,8-diethoxy-4,9-diphenyl-2,7-dioxa-5,10-diaza-3,8-diphospha-1,6(1,4)-dibenzenacyclodecaphane-3,8-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	In chloroform at 20℃;

Reference： [1]Dimukhametov, Mudaris N.; Mironov, Vladimir F.; Musin, Rashid Z. [Mendeleev Communications, 2006, vol. 16, # 1, p. 48 - 50]

19
[ 588-53-4 ]
[ 822-39-9 ]
3,8-di(β-chloro)ethoxy-4,9-diphenyl-2,7-dioxa-5,10-diaza-3,8-diphospha-1,6(1,4)-dibenzenacyclodecaphane-3,8-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	In chloroform at 20℃;

Reference： [1]Dimukhametov, Mudaris N.; Mironov, Vladimir F.; Musin, Rashid Z. [Mendeleev Communications, 2006, vol. 16, # 1, p. 48 - 50]

20
[ 588-53-4 ]
[ 55536-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. NaOH / benzene / 2 h 2: aq. H₂SO₄ / ethanol / 24 h / Ambient temperature

Reference： [1]O'Connor, Charmian J.; Mitha, Amin S. H. [Australian Journal of Chemistry, 1986, vol. 39, # 2, p. 259 - 269]

21
[ 75-21-8 ]
[ 588-53-4 ]
C₃₃H₅₁NO₁₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.2%	With potassium hydroxide In toluene at 121.101℃; Under N₂;	2 EXAMPLE 2 EXAMPLE 2 The imine product (285 g, 1.44 mol) from Example 1, toluene (200 ml) and KOH (6 g) were charged into a one-gallon stainless steel reactor.. After being purged 3 times to 60 psi with nitrogen, the reaction mixture was heated to 250° F. and ethylene oxide (635 g, 14.4 mol) was added over a period of 2 hours.. The mixture was then cooled down to room temperature and the toluene was stripped to yield 910 g (98.2%) of pale brown yellow liquid product polyethylene glycol imine (structure above).

Reference： [1]Current Patent Assignee: MILLIKEN & COMPANY - US6667392, 2003, B2 Location in patent: Page column 5

22
[ 588-53-4 ]
[ 6018-89-9 ]
bis(N-(4-hydroxyphenyl)benzaldiminato)nickel(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	In ethanol Ni-compd. in EtOH added to imine-compd. in EtOH, refluxed for 2 h; filtered hot, cooled to room temp., washed with EtOH and ether, dried invac., elem. anal.;

Reference： [1]De, Rajib Lal; Mandal, Mahuya; Roy, Lovely; Mukherjee, Jaydeep [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2008, vol. 47, # 2, p. 207 - 213]

23
[ 588-53-4 ]
[ 5970-45-6 ]
bis(N-(4-hydroxyphenyl)benzaldiminato)zinc(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	In ethanol; water Zn-compd. in EtOH-H2O (3:1 v/v) added to imine-compd. in EtOH, refluxed for 2 h; filtered hot, cooled to room temp., washed with EtOH and ether, dried invac., elem. anal.;

Reference： [1]De, Rajib Lal; Mandal, Mahuya; Roy, Lovely; Mukherjee, Jaydeep [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2008, vol. 47, # 2, p. 207 - 213]

24
[ 588-53-4 ]
[ 6046-93-1 ]
bis(N-(4-hydroxyphenyl)benzaldiminato)copper(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In ethanol Zn-compd. in EtOH added to imine-compd. in EtOH, refluxed for 2 h; filtered hot, cooled to room temp., washed with EtOH and ether, dried invac., elem. anal.;

Reference： [1]De, Rajib Lal; Mandal, Mahuya; Roy, Lovely; Mukherjee, Jaydeep [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2008, vol. 47, # 2, p. 207 - 213]

25
[ 588-53-4 ]
[ 6147-53-1 ]
bis(N-(4-hydroxyphenyl)benzaldiminato)cobalt(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In ethanol Co-compd. in EtOH added to imine-compd. in EtOH, refluxed for 2 h; filtered hot, cooled to room temp., washed with EtOH and ether, dried invac., elem. anal.;

Reference： [1]De, Rajib Lal; Mandal, Mahuya; Roy, Lovely; Mukherjee, Jaydeep [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2008, vol. 47, # 2, p. 207 - 213]

26
[ 588-53-4 ]
[ 141-97-9 ]
[ 1172631-47-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	With toluene-4-sulfonic acid Microwave irradiation;

Reference： [1]Location in patent: experimental part Kumar, B. R. Prashantha; Masih, Pankaj; Lukose, Chris Raju; Abraham, Nimmy; Priya; Xavier, Rinu Mary; Saji, Kesiya; Adhikary, Laxmi [Journal of Heterocyclic Chemistry, 2009, vol. 46, # 2, p. 336 - 339]

27
[ 588-53-4 ]
[ 100-39-0 ]
[ 6373-46-2 ]

Yield	Reaction Conditions	Operation in experiment
76.4%	Stage #1: 4-benzylidenamino-phenol; benzyl bromide With potassium carbonate In acetone for 20h; Reflux; Stage #2: With hydrogenchloride In dichloromethane; water for 1h;

Reference： [1]Location in patent: experimental part Wang, Renchao; Xu, Jiaxi [ARKIVOC, 2010, vol. 2010, # 9, p. 293 - 299]

28
[ 123-30-8 ]
[ 100-51-6 ]
[ 103-14-0 ]
[ 588-53-4 ]

Reference： [1]Green Chemistry,2010,vol. 12,p. 1281 - 1287

29
[ 617-35-6 ]
[ 588-53-4 ]
[ 24682-25-5 ]

Yield	Reaction Conditions	Operation in experiment
	With indium chloride In acetonitrile at 90℃; for 0.45h; Microwave irradiation;	21.1 (1) Indium chloride (0.4977 g, 2.25 mmol) and ethyl pyruvate (1.3064 g, 11.3 mmol) were added to an acetonitrile (15.0 mL) solution of 4-benzylideneaminophenol (0.8875 g, 4.50 mmol), and the mixture was heated with stirring at 90°C for 27 minutes with microwave irradiation. To the reaction solution, water and saturated saline were added. The mixture was subjected to extraction with dichloromethane and dried over anhydrous sodium sulfate, and then, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography, and the solvent was distilled off to obtain 6-hydroxy-2-phenyl-4-quinolinecarboxylic acid ethyl ester (0.264 g, 0.900 mmol) as a pale yellow powder. ES-MS (m/z): 294 (M + H)+.

Reference： [1]Current Patent Assignee: GENERAL ASSOCIATION PHARMA VALLEY PRO; SHIZUOKA PREFECTURE; KUMAMOTO HEALTH SCIENCE UNIVERSITY; YAKULT HONSHA CO LTD - EP2325181, 2011, A1 Location in patent: Page/Page column 64

30
[ 588-53-4 ]
[ 1204212-72-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: indium chloride / acetonitrile / 0.45 h / 90 °C / Microwave irradiation 2: sodium hydroxide; water / tetrahydrofuran / 3 h / 20 °C

Reference： [1]Current Patent Assignee: GENERAL ASSOCIATION PHARMA VALLEY PRO; SHIZUOKA PREFECTURE; KUMAMOTO HEALTH SCIENCE UNIVERSITY; YAKULT HONSHA CO LTD - EP2325181, 2011, A1

31
[ 1201-93-0 ]
[ 588-53-4 ]
3,5-dibenzoyl-1-(p-hydroxyphenyl)-4-phenyl-1,4-dihydropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With acetic acid for 2h; Reflux;

Reference： [1]Al-Awadi, Nouria A.; Ibrahim, Maher R.; Elnagdi, Mohamed H.; John, Elizabeth; Ibrahim, Yehia A. [Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 441 - 447]

32
[ 588-53-4 ]
[ 7585-39-9 ]
C₄₂H₇₀O₃₅*C₁₃H₁₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; dimethyl sulfoxide at 20℃; for 24h;

Reference： [1]Fernandes, Sergio Antonio; Do Couto Tavares, Eder; Teixeira, Robson Ricardo; Da Silva, Cleiton Moreira; Montanari, Ricardo Marques; De Fatima, Angelo; Anconi, Cleber Paulo Andrada; De Almeida, Wagner Batista; Dos Santos, Helio Ferreira; Da Silva, Antonio Alberto [Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2013, vol. 75, # 1-2, p. 197 - 204]

33
[ 588-53-4 ]
[ 137407-62-6 ]
C₅₆H₄₈O₃₂S₈*C₁₃H₁₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; dimethyl sulfoxide at 20℃; for 24h;

Reference： [1]Fernandes, Sergio Antonio; Do Couto Tavares, Eder; Teixeira, Robson Ricardo; Da Silva, Cleiton Moreira; Montanari, Ricardo Marques; De Fatima, Angelo; Anconi, Cleber Paulo Andrada; De Almeida, Wagner Batista; Dos Santos, Helio Ferreira; Da Silva, Antonio Alberto [Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2013, vol. 75, # 1-2, p. 197 - 204]

34
[ 588-53-4 ]
[ 134-81-6 ]
4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With ammonium acetate In neat (no solvent) for 0.216667h; Microwave irradiation; Green chemistry;

Reference： [1]Sharma, Gyanendra Kumar; Sharma, Naveen Kumar; Pathak, Devender [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 2, p. 266 - 272]

35
[ 588-53-4 ]
[ 1225020-90-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: aluminum potassium sulfate dodecahydrate / acetonitrile / 8 h / 20 °C 2.1: thionyl chloride / toluene / 1.5 h / Reflux 2.2: 0.5 h / 100 °C 3.1: potassium carbonate / acetone / 12 h / Reflux