[ CAS No. 5463-50-3 ] {[proInfo.proName]}

Name: 5463-50-3|4,7-Dimethylisobenzofuran-1,3-dione|97%
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SKU: A625746
Price: 79.0 USD
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Quality Control of [ 5463-50-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 5463-50-3 ]

CAS No. :	5463-50-3	MDL No. :	MFCD00094951
Formula :	C₁₀H₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WEPCDISQBQXOBE-UHFFFAOYSA-N
M.W :	176.17	Pubchem ID :	21616
Synonyms :

Safety of [ 5463-50-3 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P261-P264-P270-P271-P272-P280-P285-P301+P312-P302+P352-P304+P340-P305+P351+P338-P310-P321-P330-P333+P313-P362-P403+P233-P405-P501	UN#:	2923
Hazard Statements:	H302-H315-H317-H318-H334-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 5463-50-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 5463-50-3 ]

[ 5463-50-3 ] Synthesis Path-Downstream 1~87

1
[ 5463-50-3 ]
[ 533-73-3 ]
1,2,4-trihydroxy-5,8-dimethyl-anthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride; sodium chloride at 160 - 180℃;

Reference： [1]Mayer; Stark [Chemische Berichte, 1931, vol. 64, p. 2003,2007] Stark,O. [Diss.<Frankfurt 1930> S.58]

2
[ 5463-50-3 ]
[ 34589-46-3 ]
[ 2346-65-8 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether; benzene

Reference： [1]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]

3
[ 5463-50-3 ]
phenylmagnesium bromide [ No CAS ]
[ 2346-61-4 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether; benzene

Reference： [1]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]

4
[ 5463-50-3 ]
[ 108-38-3 ]
[ 2346-65-8 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride

Reference： [1]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]

5
[ 5463-50-3 ]
[ 123-31-9 ]
[ 170685-35-5 ]

Yield	Reaction Conditions	Operation in experiment
36%	With aluminium trichloride; sodium chloride solid phase reaction;
	With aluminium trichloride; sodium chloride at 190℃;

Reference： [1]Kotha, Sambasivarao; Stoodley, Richard J. [Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 3, p. 621 - 624]
[2]Mayer; Stark [Chemische Berichte, 1931, vol. 64, p. 2003,2007]

6
[ 5463-50-3 ]
[ 108-67-8 ]
[ 2346-69-2 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride

Reference： [1]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]

7
[ 5463-50-3 ]
[ 87-66-1 ]
[ 860732-94-1 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride; sodium chloride at 140 - 175℃;

Reference： [1]Mayer; Stark [Chemische Berichte, 1931, vol. 64, p. 2003,2007] Stark,O. [Diss.<Frankfurt 1930> S.59]

8
[ 5463-50-3 ]
[ 71-43-2 ]
[ 2346-61-4 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride; 1,1,2,2-tetrachloroethane

Reference： [1]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]

9
[ 5463-50-3 ]
[ 2633-66-1 ]
[ 2346-69-2 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether; benzene

Reference： [1]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]

10
[ 5463-50-3 ]
[ 54598-91-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With hydrogenchloride; mercury dichloride; zinc In acetic acid for 4h; Heating;
	With lithium aluminium tetrahydride; diethyl ether

Reference： [1]Setiabudi, Frans; Boldt, Peter [Liebigs Annalen der Chemie, 1985, # 6, p. 1272 - 1279]
[2]Buchta; Loew [Justus Liebigs Annalen der Chemie, 1955, vol. 597, p. 123]

11
[ 5463-50-3 ]
[ 476-73-3 ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid at 130 - 140℃; im Rohr;
	With nitric acid at 140℃;

Reference： [1]Freund; Fleischer [Justus Liebigs Annalen der Chemie, 1916, vol. 411, p. 33]
[2]Alder; Vogt [Justus Liebigs Annalen der Chemie, 1951, vol. 571, p. 137,146]

12
2,5-dimethylphthalic anhydride [ No CAS ]
[ 5463-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid at 100℃;

Reference： [1]Diels; Alder [Chemische Berichte, 1929, vol. 62, p. 560]

13
[ 944-38-7 ]
[ 5463-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	Erhitzen ueber ihren Schmelzpunkt;
	at 100 - 130℃; Yield given;
	In water at 60℃;

Reference： [1]Gucci; Grassi-Cristaldi [Gazzetta Chimica Italiana, 1892, vol. 22 I, p. 44]
[2]Dmowski, Wojciech [Journal of Fluorine Chemistry, 1993, vol. 65, # 1-2, p. 139 - 142]
[3]Eberson,L.; Welinder,H. [Journal of the American Chemical Society, 1971, vol. 93, # 22, p. 5821 - 5826]

14
3,6-dimethyl-cyclohexa-2,6-diene-1,2-dicarboxylic acid-anhydride [ No CAS ]
[ 5463-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid at 100℃;

Reference： [1]Diels; Alder [Chemische Berichte, 1929, vol. 62, p. 560]

15
[ 36337-42-5 ]
[ 5463-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfur at 230℃;

Reference： [1]Alder; Vogt [Justus Liebigs Annalen der Chemie, 1951, vol. 571, p. 137,146]

16
[ 5463-50-3 ]
[ 38108-81-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With lithium aluminium tetrahydride In tetrahydrofuran at 22 - 70℃; for 18h; Inert atmosphere;
84%	Stage #1: 3,6-dimethyl phthalic anhydride With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 1.25h; Heating / reflux; Stage #2: With sodium hydroxide; water at 0℃;	1 A 1 L 3-necked RBF is charged with a 1.0M lithium aluminium hydride solution in tetrahydrofuran (175 mL, 0.175 mol) and anhydrous tetrahydrofuran (100 mL) under nitrogen. The solution is cooled to -780C and a solution of 1 ,7-dimethyl-4,10-dioxa-tricyclo[5.2.1.0 ]dec-8-ene-3,5- dione 2 (12.3 g, 0.070 mol) in anhydrous tetrahydrofuran (150 mL) is added from a dropping funnel over a period of 30 minutes The reaction mixture is heated to reflux and stirred for 45 h. The reaction mixture is cooled to O0C using an ice bath and 2M sodium hydroxide solution (20 mL) is slowly added dropwise. The mixture is allowed to warm up to 22°C and the precipitate is filtered off and washed thoroughly with diethyl ether and tetrahydrofuran. The filtrate is concentrated in vacuo. Recrystallisation from ethyl acetate/petrol 40-60 (1/5) yielded the product 3 as colourless needles (9.70 g, 84%): 1H-NMR (300 MHz, CDCI3) δ 7.07 (s, 2H), 4.77 (s, 4H), 2.39 (s, 6H).
70%	With lithium aluminium tetrahydride In tetrahydrofuran for 12h; Heating;

70%	With lithium aluminium tetrahydride In tetrahydrofuran Reflux; Inert atmosphere;
63.5%	With lithium aluminium tetrahydride In tetrahydrofuran at -5 - 20℃; Inert atmosphere;	1.3 Step 3: Synthesis of 1,2-bis(hydroxymethyl)-3,6-dimethylbenzene Under nitrogen protection, 90ml lithium aluminum tetrahydride solution (2N) mixed with 180 ml tetrahydrofuran, and cooling to -5 °C, 12.34 g of 4,7-dimethyl-isobenzofuran-1,3-dione dissolved in 134 ml of tetrahydrofuran, and add it into the reaction flask within 1.5 hours, after that naturally rise at room temperature, after reaching at room temperature, heating is started and the reaction solution is refluxed overnight; reached at 0 °C, slowly add 2M sodium hydroxide solution, after that naturally rise at 5 °C, obtained solid, filter, obtained 7.4g product, yield 63.5%.
58%	With lithium aluminium tetrahydride In tetrahydrofuran for 48h; Heating;
	With lithium aluminium tetrahydride In diethyl ether
	Multi-step reaction with 2 steps 1: lithium alanate; diethyl ether 2: LiAlH₄; diethyl ether
	With lithium aluminium tetrahydride In tetrahydrofuran for 20h; Reflux;

Reference： [1]Abel, Brooks A.; Lidston, Claire A. L.; Coates, Geoffrey W. [Journal of the American Chemical Society, 2019, vol. 141, # 32, p. 12760 - 12769]
[2]Current Patent Assignee: MERCK KGAA - WO2008/128618, 2008, A1 Location in patent: Page/Page column 32; 7; 9; Sheet 1; Sheet 2; Sheet4
[3]Rubottom, G. M.; Wey, J. E. [Synthetic Communications, 1984, vol. 14, # 6, p. 507 - 514]
[4]Llorente, Gonzalo Rincon; Dufourg-Madec, Marie-Beatrice; Crouch, David J.; Pritchard, Robin G.; Ogier, Simon; Yeates, Stephen G. [Chemical Communications, 2009, # 21, p. 3059 - 3061]
[5]Current Patent Assignee: HANGZHOU SFT NEW MATERIAL TECH - CN107935804, 2018, A Location in patent: Paragraph 0021; 0023; 0038; 0043
[6]Lachapele, A.; St-Jacques, M. [Canadian Journal of Chemistry, 1985, vol. 63, p. 2185 - 2191]
[7]Brickwood,D.J. et al. [Journal of the Chemical Society. Perkin transactions I, 1978, p. 1398 - 1414]
[8]Buchta; Loew [Justus Liebigs Annalen der Chemie, 1955, vol. 597, p. 123]
[9]Kitamura, Chitoshi; Naito, Takao; Yoneda, Akio; Kawase, Takeshi; Komatsu, Toshiki [Chemistry Letters, 2010, vol. 39, # 7, p. 771 - 773]

17
[ 5463-50-3 ]
[ 944-38-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 3,6-dimethyl phthalic anhydride With water; potassium hydroxide Stage #2: With hydrogenchloride; water
	In water at 60℃; other solvent, other temperature;

Reference： [1]Shiramizu, Mika; Toste, F. Dean [Chemistry - A European Journal, 2011, vol. 17, # 44, p. 12452 - 12457]
[2]Eberson,L.; Welinder,H. [Journal of the American Chemical Society, 1971, vol. 93, # 22, p. 5821 - 5826]

18
[ 625-86-5 ]
[ 108-31-6 ]
[ 5463-50-3 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sulfuric acid Ambient temperature;
55%	Stage #1: 2,5-dimethylfuran; maleic anhydride In diethyl ether Inert atmosphere; Stage #2: With sulfuric acid In diethyl ether Inert atmosphere;
	With sulfuric acid 1.) Et₂O, 25 deg C, 4.5 h, 2.) -6 - 0 deg C, 1 h; Yield given. Multistep reaction;

Reference： [1]Pakusch, Joachim; Ruechardt, Christoph [Chemische Berichte, 1990, vol. 123, # 11, p. 2147 - 2151]
[2]Location in patent: scheme or table Cao, Dennis; Wang, Cheng; Giesener, Marc A.; Liu, Zhichang; Stoddart, J. Fraser [Chemical Communications, 2012, vol. 48, # 54, p. 6791 - 6793]
[3]Huang, Nai Zheng; Jia, Jian Hua; Wang, Li Li; Chan, Tze-Lock; Mak, Thomas C. W. [Tetrahedron Letters, 1982, vol. 23, # 46, p. 4797 - 4800]

19
[ 5463-50-3 ]
[ 106-42-3 ]
[ 85217-64-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With aluminium trichloride at 65℃; for 4h;
	With aluminum (III) chloride at 0 - 63℃; for 5h;

Reference： [1]Huang, Nai Zheng; Jia, Jian Hua; Wang, Li Li; Chan, Tze-Lock; Mak, Thomas C. W. [Tetrahedron Letters, 1982, vol. 23, # 46, p. 4797 - 4800]
[2]Barman, Samir; Anand Garg, Jai; Blacque, Olivier; Venkatesan, Koushik; Berke, Heinz [Chemical Communications, 2012, vol. 48, # 90, p. 11127 - 11129]

20
[ 5463-50-3 ]
[ 585-34-2 ]
[ 79563-76-1 ]

Yield	Reaction Conditions	Operation in experiment
15%	With aluminium trichloride In carbon disulfide at 38℃;
15%	With aluminium trichloride In carbon disulfide 1) 15h, 38 deg C, 2) 30h, r.t.;

Reference： [1]Setiabudi, Frans; Boldt, Peter [Tetrahedron Letters, 1981, vol. 22, # 30, p. 2863 - 2864]
[2]Setiabudi, Frans; Boldt, Peter [Liebigs Annalen der Chemie, 1985, # 6, p. 1272 - 1279]

21
[ 5463-50-3 ]
[ 553-94-6 ]
[ 57380-70-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With magnesium In diethyl ether; toluene
	(i) Mg, (ii) /BRN= 141713/; Multistep reaction;

Reference： [1]Pakusch, Joachim; Ruechardt, Christoph [Chemische Berichte, 1990, vol. 123, # 11, p. 2147 - 2151]
[2]Carruthers,W. [Journal of the Chemical Society, 1963, p. 5551 - 5552]

22
[ 5463-50-3 ]
[ 1099-45-2 ]
[ 84641-80-5 ]
[ 84641-81-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 75% 2: 5%	In chloroform for 12h; Heating;

Reference： [1]Abell, Andrew D.; Massy-Westropp Ralph A. [Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2077 - 2087]

23
[ 5463-50-3 ]
[ 15540-88-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With formamide at 150℃; for 2h;

Reference： [1]Hennige, Hans; Kreher, Richard P.; Konrad, Michael; Jelitto, Frank [Chemische Berichte, 1988, vol. 121, p. 243 - 252]

24
[ 5463-50-3 ]
[ 85217-64-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With aluminium trichloride In xylene at 60 - 65℃; for 4h;

Reference： [1]Chan, Tze-Lock; Mak, Thomas C. W.; Poon, Chi-Duen; Wong, Henry N. C.; Jia, Jian Hua; Wang, Li Li [Tetrahedron, 1986, vol. 42, # 2, p. 655 - 662]

25
[ 5463-50-3 ]
[ 116349-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate In methanol at -40℃;

Reference： [1]Krohn, Karsten; Rieger, Hagen; Broser, Erwin; Schiess, Peter; Chen, Shizhi; Strubin, Thomas [Liebigs Annalen der Chemie, 1988, p. 943 - 948]

26
[ 77880-59-2 ]
[ 5463-50-3 ]

Yield	Reaction Conditions	Operation in experiment
63%	With sulfuric acid at 0℃; for 2h;
58%	With sulfuric acid at -6 - 0℃;
50%	With sulfuric acid at -6 - 0℃;

45%	With sulfuric acid 1) 1 h, 0 deg C; 2) 30 min, 10 deg C;
33%	With sulfuric acid at 10℃; Cooling with ice;	3.B (B) Synthesis of 3,6-dimethylphthalic anhydride (2) To concentrated ice-cooled concentrated sulfuric acid (56.4 ml), compound 1 (15.3 g) was dissolved little by little with stirring so that the temperature of the concentrated sulfuric acid did not exceed 10 ° C. After Complete Addition of Compound 1 was finished, the reaction solution was further stirred for 2 hours under ice cooling. The reaction solution was poured onto 300 g of ice, and the precipitate that precipitated was collected by filtration, washed with ice-cold water and lyophilized to obtain the objective compound 2 as a pale yellow powder (7.7 g, yield 33%) Obtained
	With sulfuric acid
	With sulfuric acid at 0℃; for 1h;
	With sulfuric acid at -6 - 0℃;

Reference： [1]Shiramizu, Mika; Toste, F. Dean [Chemistry - A European Journal, 2011, vol. 17, # 44, p. 12452 - 12457]
[2]Chan, Tze-Lock; Mak, Thomas C. W.; Poon, Chi-Duen; Wong, Henry N. C.; Jia, Jian Hua; Wang, Li Li [Tetrahedron, 1986, vol. 42, # 2, p. 655 - 662]
[3]Llorente, Gonzalo Rincon; Dufourg-Madec, Marie-Beatrice; Crouch, David J.; Pritchard, Robin G.; Ogier, Simon; Yeates, Stephen G. [Chemical Communications, 2009, # 21, p. 3059 - 3061]
[4]Hennige, Hans; Kreher, Richard P.; Konrad, Michael; Jelitto, Frank [Chemische Berichte, 1988, vol. 121, p. 243 - 252]
[5]Current Patent Assignee: NAGASAKI UNIVERSITY - JP2016/193897, 2016, A Location in patent: Paragraph 0044-0047
[6]Lachapele, A.; St-Jacques, M. [Canadian Journal of Chemistry, 1985, vol. 63, p. 2185 - 2191]
[7]Kitamura, Chitoshi; Naito, Takao; Yoneda, Akio; Kawase, Takeshi; Komatsu, Toshiki [Chemistry Letters, 2010, vol. 39, # 7, p. 771 - 773]
[8]Barman, Samir; Anand Garg, Jai; Blacque, Olivier; Venkatesan, Koushik; Berke, Heinz [Chemical Communications, 2012, vol. 48, # 90, p. 11127 - 11129]

27
[ 77079-34-6 ]
[ 5463-50-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With pyridine In 1,4-dioxane a few minutes;

Reference： [1]Schoen, Georg; Hopf, Henning [Liebigs Annalen der Chemie, 1981, # 1, p. 165 - 180]

28
[ 5463-50-3 ]
[ 2416-94-6 ]
[ 198777-87-6 ]

Yield	Reaction Conditions	Operation in experiment
51%	With aluminium trichloride In 1,2-dichloro-benzene at 70℃; for 24h;

Reference： [1]Boldt; Knoblauch; Riemenschneider [Journal fur Praktische Chemie - Chemiker-Zeitung, 1997, vol. 339, # 7, p. 646 - 649]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid

30
[ 5463-50-3 ]
[ 367-25-9 ]
2-(2,4-difluorophenyl)-4,7-dimethyl-1H-isoindole-1,3(2H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	In acetic acid for 3.5h; Heating;

Reference： [1]Gütschow, Michael; Hecker, Thomas; Thiele, Andrea; Hauschildt, Sunna; Eger, Kurt [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 4, p. 1059 - 1065]

31
4,7-dimethyl-3a,4,7,7a-tetrahydro-4,7-epoxyisobenzofuran-1,3-dione [ No CAS ]
[ 5463-50-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sulfuric acid at -5 - 22℃; for 0.5h;	1 1 ,7-Dimethyl-4,10-dioxa-tricyclo[5.2.1.0 ]dec-8-ene-3,5-dione 1 (30.0 g, 0.150 mol) is added slowly in portions to stirred 98% sulfuric acid (300 mL) in a 1 L flange flask cooled to -50C using a salt-ice bath - note that the temperature is kept below O0C during the addition. The mixture is stirred for 30 mins at -50C and then allowed to warm up to 22°C. The mixture is carefully poured onto crushed ice (1.5 L). The cream precipitate that formed is filtered off and washed with ice water. The precipitate is dissolved in a 5% aq. sodium hydroxide solution (225 mL) with stirring. Glacial acetic acid (20 mL) is added slowly to the stirred solution. A cream precipitate forms and this is filtered off and discarded. 37% Hydrochloric acid (50 mL) is added to the stirred filtrate and the mixture is stirred for 2 h during which time a precipitate is formed. The precipitate is filtered off and dried in the vacuum oven overnight to yield the product as a cream solid (11.13 g, 41 %). The filtrate is allowed to stand overnight during which time further product precipitated out. The second crop of precipitate is filtered off and dried under vacuum to yield the product 2 as a cream solid (5.79 g, 21 %): 1H-NMR (300 MHz, CDCI3) δ 7.18 (s, 2H), 2.40 (s, 6H).
56%	With sulfuric acid

Reference： [1]Current Patent Assignee: MERCK KGAA - WO2008/128618, 2008, A1 Location in patent: Page/Page column 31-32; 7; 9; Sheet 1; Sheet 2; Sheet 4
[2]Kotha, Sambasivarao; Stoodley, Richard J. [Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 3, p. 621 - 624]

32
[ 625-86-5 ]
[ 5463-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 96 percent / diethyl ether 2: 56 percent / H₂SO₄
	Multi-step reaction with 2 steps 1: 87 percent / 5.5 h / Ambient temperature 2: 45 percent / 90 percent H₂SO₄ / 1) 1 h, 0 deg C; 2) 30 min, 10 deg C
	Multi-step reaction with 2 steps 1: 83 percent / diethyl ether / 2.5 h / 25 °C 2: 58 percent / concd. H₂SO₄ / -6 - 0 °C

	Multi-step reaction with 2 steps 1: diethyl ether / 3 h / 20 °C 2: sulfuric acid / 1 h / 0 °C
	Multi-step reaction with 2 steps 1: diethyl ether / 20 °C 2: sulfuric acid / 2 h / 0 °C
	Multi-step reaction with 2 steps 1: diethyl ether / 2.5 h / 20 °C 2: sulfuric acid / -6 - 0 °C
	Multi-step reaction with 2 steps 1: diethyl ether / 3 h / Inert atmosphere 2: sulfuric acid / 10 °C / Cooling with ice
	Multi-step reaction with 2 steps 1: tert-butyl methyl ether / 44 h / 15 - 23 °C / Large scale 2: sulfuric acid / tetrahydrofuran / 1 h / -5 - 20 °C / Large scale
	Multi-step reaction with 2 steps 1: diethyl ether / 3 h / 22 °C 2: sulfuric acid / 3.5 h / -20 - 0 °C

Reference： [1]Kotha, Sambasivarao; Stoodley, Richard J. [Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 3, p. 621 - 624]
[2]Hennige, Hans; Kreher, Richard P.; Konrad, Michael; Jelitto, Frank [Chemische Berichte, 1988, vol. 121, p. 243 - 252]
[3]Chan, Tze-Lock; Mak, Thomas C. W.; Poon, Chi-Duen; Wong, Henry N. C.; Jia, Jian Hua; Wang, Li Li [Tetrahedron, 1986, vol. 42, # 2, p. 655 - 662]
[4]Kitamura, Chitoshi; Naito, Takao; Yoneda, Akio; Kawase, Takeshi; Komatsu, Toshiki [Chemistry Letters, 2010, vol. 39, # 7, p. 771 - 773]
[5]Shiramizu, Mika; Toste, F. Dean [Chemistry - A European Journal, 2011, vol. 17, # 44, p. 12452 - 12457]
[6]Barman, Samir; Anand Garg, Jai; Blacque, Olivier; Venkatesan, Koushik; Berke, Heinz [Chemical Communications, 2012, vol. 48, # 90, p. 11127 - 11129]
[7]Current Patent Assignee: NAGASAKI UNIVERSITY - JP2016/193897, 2016, A
[8]Current Patent Assignee: HANGZHOU SFT NEW MATERIAL TECH - CN107935804, 2018, A
[9]Abel, Brooks A.; Lidston, Claire A. L.; Coates, Geoffrey W. [Journal of the American Chemical Society, 2019, vol. 141, # 32, p. 12760 - 12769]

33
[ 5463-50-3 ]
[ 405218-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 36 percent / AlCl₃; NaCl / solid phase reaction 2: 6.7 g / Pb(OAc)4 / acetic acid / 2 h / 20 °C

Reference： [1]Kotha, Sambasivarao; Stoodley, Richard J. [Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 3, p. 621 - 624]

34
[ 5463-50-3 ]
C₁₆H₁₀O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 36 percent / AlCl₃; NaCl / solid phase reaction 2: 6.7 g / Pb(OAc)4 / acetic acid / 2 h / 20 °C 3: 3.2 g / m-cloroperoxybenzoic acid / CH₂Cl₂ / 4 h / 20 °C

Reference： [1]Kotha, Sambasivarao; Stoodley, Richard J. [Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 3, p. 621 - 624]

35
[ 5463-50-3 ]
C₃₄H₃₄O₁₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 36 percent / AlCl₃; NaCl / solid phase reaction 2: 6.7 g / Pb(OAc)4 / acetic acid / 2 h / 20 °C 3: 3.2 g / m-cloroperoxybenzoic acid / CH₂Cl₂ / 4 h / 20 °C 4: acetone / 60 h / 20 °C 5: 0.525 g / HCl / tetrahydrofuran / 0.5 h

Reference： [1]Kotha, Sambasivarao; Stoodley, Richard J. [Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 3, p. 621 - 624]

36
[ 5463-50-3 ]
C₃₇H₄₂O₁₆Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 36 percent / AlCl₃; NaCl / solid phase reaction 2: 6.7 g / Pb(OAc)4 / acetic acid / 2 h / 20 °C 3: 3.2 g / m-cloroperoxybenzoic acid / CH₂Cl₂ / 4 h / 20 °C 4: acetone / 60 h / 20 °C

Reference： [1]Kotha, Sambasivarao; Stoodley, Richard J. [Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 3, p. 621 - 624]

37
[ 5463-50-3 ]
1,3,4,5,8-pentamethyl-9,10-dihydro-2-anthracenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 51 percent / AlCl₃ / 1,2-dichloro-benzene / 24 h / 70 °C 2: 18 percent / Zn-Hg, conc. HCl / ethanol / 3 h / Heating

Reference： [1]Boldt; Knoblauch; Riemenschneider [Journal fur Praktische Chemie - Chemiker-Zeitung, 1997, vol. 339, # 7, p. 646 - 649]

38
[ 5463-50-3 ]
[ 198777-91-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 51 percent / AlCl₃ / 1,2-dichloro-benzene / 24 h / 70 °C 2: 53 percent / Zn-Hg, conc. HCl / aq. acetic acid / 1.5 h / Heating

Reference： [1]Boldt; Knoblauch; Riemenschneider [Journal fur Praktische Chemie - Chemiker-Zeitung, 1997, vol. 339, # 7, p. 646 - 649]

39
[ 5463-50-3 ]
3-(4-hydroxy-2,3,5-trimethylphenyl)-4,7-dimethyl-1,3-dihydro-1-isobenzofuranone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 51 percent / AlCl₃ / 1,2-dichloro-benzene / 24 h / 70 °C 2: 42 percent / Zn-Hg, conc. HCl / aq. acetic acid / 2 h / Heating

Reference： [1]Boldt; Knoblauch; Riemenschneider [Journal fur Praktische Chemie - Chemiker-Zeitung, 1997, vol. 339, # 7, p. 646 - 649]

40
[ 5463-50-3 ]
methyl 2-(4-hydroxy-2,3,5-trimethylbenzoyl)-3,6-dimethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 51 percent / AlCl₃ / 1,2-dichloro-benzene / 24 h / 70 °C 2: 4.0 g / TFA / 0.17 h / Heating

Reference： [1]Boldt; Knoblauch; Riemenschneider [Journal fur Praktische Chemie - Chemiker-Zeitung, 1997, vol. 339, # 7, p. 646 - 649]

41
[ 37902-49-1 ]
[ 5463-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 20percent KOH / H₂O / 1.) 80 deg C, 2 h, 2.) r.t., overnight 2: 100 - 130 °C / 0.5 Torr

Reference： [1]Dmowski, Wojciech [Journal of Fluorine Chemistry, 1993, vol. 65, # 1-2, p. 139 - 142]

42
[ 5463-50-3 ]
[ 38108-82-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 70 percent / LAH / tetrahydrofuran / 12 h / Heating 2: 96 percent / PBr₃ / benzene / 1.) room temperature, 1 h, 2.) 40 deg C, 1 h
	Multi-step reaction with 3 steps 1: lithium alanate; diethyl ether 2: LiAlH₄; diethyl ether 3: benzene; phosphorus (III)-bromide
	Multi-step reaction with 2 steps 1: LiAlH₄ / diethyl ether 2: PBr₃ / diethyl ether; benzene

	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / -5 - 20 °C / Inert atmosphere 2: phosphorus tribromide / toluene / 3.5 h / 20 - 40 °C
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 22 - 70 °C / Inert atmosphere 2: phosphorus tribromide / diethyl ether / 18 h / 22 °C

Reference： [1]Rubottom, G. M.; Wey, J. E. [Synthetic Communications, 1984, vol. 14, # 6, p. 507 - 514]
[2]Buchta; Loew [Justus Liebigs Annalen der Chemie, 1955, vol. 597, p. 123]
[3]Brickwood,D.J. et al. [Journal of the Chemical Society. Perkin transactions I, 1978, p. 1398 - 1414]
[4]Current Patent Assignee: HANGZHOU SFT NEW MATERIAL TECH - CN107935804, 2018, A
[5]Abel, Brooks A.; Lidston, Claire A. L.; Coates, Geoffrey W. [Journal of the American Chemical Society, 2019, vol. 141, # 32, p. 12760 - 12769]

43
[ 5463-50-3 ]
[ 32667-76-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 70 percent / LAH / tetrahydrofuran / 12 h / Heating 2: 96 percent / PBr₃ / benzene / 1.) room temperature, 1 h, 2.) 40 deg C, 1 h 3: 73 percent / zinc/silver couple / dimethylformamide

Reference： [1]Rubottom, G. M.; Wey, J. E. [Synthetic Communications, 1984, vol. 14, # 6, p. 507 - 514]

44
[ 5463-50-3 ]
[ 38108-84-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 70 percent / LAH / tetrahydrofuran / 12 h / Heating 2: 96 percent / PBr₃ / benzene / 1.) room temperature, 1 h, 2.) 40 deg C, 1 h 3: 73 percent / zinc/silver couple / dimethylformamide 4: 69 percent / diethyl ether / 12 h / Ambient temperature

Reference： [1]Rubottom, G. M.; Wey, J. E. [Synthetic Communications, 1984, vol. 14, # 6, p. 507 - 514]

45
[ 5463-50-3 ]
[ 92921-66-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 70 percent / LAH / tetrahydrofuran / 12 h / Heating 2: 96 percent / PBr₃ / benzene / 1.) room temperature, 1 h, 2.) 40 deg C, 1 h 3: 74 percent / zinc/silver couple / dimethylformamide

Reference： [1]Rubottom, G. M.; Wey, J. E. [Synthetic Communications, 1984, vol. 14, # 6, p. 507 - 514]

46
[ 5463-50-3 ]
5,8-dimethyl-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic acid anhydride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 70 percent / LAH / tetrahydrofuran / 12 h / Heating 2: 96 percent / PBr₃ / benzene / 1.) room temperature, 1 h, 2.) 40 deg C, 1 h 3: 70 percent / zinc/silver couple / dimethylformamide

Reference： [1]Rubottom, G. M.; Wey, J. E. [Synthetic Communications, 1984, vol. 14, # 6, p. 507 - 514]

47
[ 5463-50-3 ]
[ 110568-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 93 percent / formamide / 2 h / 150 °C 2: 67 percent / Sn/HCl / 5 h / Heating

Reference： [1]Hennige, Hans; Kreher, Richard P.; Konrad, Michael; Jelitto, Frank [Chemische Berichte, 1988, vol. 121, p. 243 - 252]

48
[ 5463-50-3 ]
[ 110568-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 93 percent / formamide / 2 h / 150 °C 2: 67 percent / Sn/HCl / 5 h / Heating 3: 93 percent / CH₂Cl₂ / 20 h / Ambient temperature

Reference： [1]Hennige, Hans; Kreher, Richard P.; Konrad, Michael; Jelitto, Frank [Chemische Berichte, 1988, vol. 121, p. 243 - 252]

49
[ 5463-50-3 ]
[ 116324-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: NaBH₄ / methanol / -40 °C 2: 1 h / Ambient temperature 3: 1.86 g / 2 h / 570 °C / 0.05 Torr 4: 2.) 2-methyl-2,4-pentanediol, glacial acetic acid / 1.) CH₂Cl₂, 4 d, day light; 2.) CH₂Cl₂, 48 h, RT

Reference： [1]Krohn, Karsten; Rieger, Hagen; Broser, Erwin; Schiess, Peter; Chen, Shizhi; Strubin, Thomas [Liebigs Annalen der Chemie, 1988, p. 943 - 948]

50
[ 5463-50-3 ]
[ 79563-77-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 15 percent / AlCl₃ / CS₂ / 1) 15h, 38 deg C, 2) 30h, r.t. 2: 68 percent / 10percent NaOH, Zn / 24 h / Heating

Reference： [1]Setiabudi, Frans; Boldt, Peter [Liebigs Annalen der Chemie, 1985, # 6, p. 1272 - 1279]

51
[ 5463-50-3 ]
[ 116324-52-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NaBH₄ / methanol / -40 °C 2: 1 h / Ambient temperature 3: 1.86 g / 2 h / 570 °C / 0.05 Torr

Reference： [1]Krohn, Karsten; Rieger, Hagen; Broser, Erwin; Schiess, Peter; Chen, Shizhi; Strubin, Thomas [Liebigs Annalen der Chemie, 1988, p. 943 - 948]

52
[ 5463-50-3 ]
Trifluoro-acetic acid 4,7-dimethyl-3-oxo-1,3-dihydro-isobenzofuran-1-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaBH₄ / methanol / -40 °C 2: 1 h / Ambient temperature

Reference： [1]Krohn, Karsten; Rieger, Hagen; Broser, Erwin; Schiess, Peter; Chen, Shizhi; Strubin, Thomas [Liebigs Annalen der Chemie, 1988, p. 943 - 948]

53
[ 5463-50-3 ]
[ 65869-19-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: NaBH₄ / methanol / -40 °C 2: 1 h / Ambient temperature 3: 1.86 g / 2 h / 570 °C / 0.05 Torr 4: 80 percent / CH₂Cl₂ / 72 h / Irradiation

Reference： [1]Krohn, Karsten; Rieger, Hagen; Broser, Erwin; Schiess, Peter; Chen, Shizhi; Strubin, Thomas [Liebigs Annalen der Chemie, 1988, p. 943 - 948]

54
[ 5463-50-3 ]
[ 99143-93-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 58 percent / LiAlH₄ / tetrahydrofuran / 48 h / Heating 2: 52 percent / thionyl chloride, triethylamine / diethyl ether / 1.5 h / 0 °C

Reference： [1]Lachapele, A.; St-Jacques, M. [Canadian Journal of Chemistry, 1985, vol. 63, p. 2185 - 2191]

55
[ 5463-50-3 ]
[ 79563-77-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 15 percent / AlCl₃ / CS₂ / 38 °C 2: 64 percent / Zn, NaOH

Reference： [1]Setiabudi, Frans; Boldt, Peter [Tetrahedron Letters, 1981, vol. 22, # 30, p. 2863 - 2864]

56
[ 5463-50-3 ]
[ 57380-69-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 75 percent / Mg / diethyl ether; toluene 2: 66 percent / Zn, NaOH / 48 h / Heating

Reference： [1]Pakusch, Joachim; Ruechardt, Christoph [Chemische Berichte, 1990, vol. 123, # 11, p. 2147 - 2151]

57
[ 5463-50-3 ]
[ 127280-60-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 75 percent / Mg / diethyl ether; toluene 2: 25 percent / Zn, NaOH / 48 h / Heating

Reference： [1]Pakusch, Joachim; Ruechardt, Christoph [Chemische Berichte, 1990, vol. 123, # 11, p. 2147 - 2151]

58
[ 5463-50-3 ]
[ 488-23-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: lithium alanate; diethyl ether 2: LiAlH₄; diethyl ether 3: benzene; phosphorus (III)-bromide 4: lithium alanate; tetrahydrofuran
	Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / -5 - 20 °C / Inert atmosphere 2: phosphorus tribromide / toluene / 3.5 h / 20 - 40 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 5 °C / Inert atmosphere; Reflux

Reference： [1]Buchta; Loew [Justus Liebigs Annalen der Chemie, 1955, vol. 597, p. 123]
[2]Current Patent Assignee: HANGZHOU SFT NEW MATERIAL TECH - CN107935804, 2018, A

59
[ 5463-50-3 ]
[ 35019-06-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aluminium chloride 2: copper-salt of/the/ 2.5-dimethyl-6-<2.4.6-trimethyl-benzoyl>-benzoic acid / 195 °C
	Multi-step reaction with 2 steps 1: benzene; diethyl ether 2: copper-salt of/the/ 2.5-dimethyl-6-<2.4.6-trimethyl-benzoyl>-benzoic acid / 195 °C

Reference： [1]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]
[2]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]

60
[ 5463-50-3 ]
[ 72181-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: benzene; diethyl ether 2: thionyl chloride / Behandeln des Reaktionsprodukts mit Methanol und Pyridin
	Multi-step reaction with 2 steps 1: aluminium chloride; 1.1.2.2-tetrachloro-ethane 2: thionyl chloride / Behandeln des Reaktionsprodukts mit Methanol und Pyridin

Reference： [1]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]
[2]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]

61
[ 5463-50-3 ]
2-(2,4-dimethyl-benzoyl)-3,6-dimethyl-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: benzene; diethyl ether 2: hydrogen chloride
	Multi-step reaction with 2 steps 1: benzene; diethyl ether 2: diethyl ether
	Multi-step reaction with 2 steps 1: aluminium chloride 2: hydrogen chloride

Multi-step reaction with 2 steps 1: aluminium chloride 2: diethyl ether

Reference： [1]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]
[2]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]
[3]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]
[4]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]

62
[ 5463-50-3 ]
[ 72181-92-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: benzene; diethyl ether 2: diethyl ether
	Multi-step reaction with 2 steps 1: aluminium chloride; 1.1.2.2-tetrachloro-ethane 2: diethyl ether

Reference： [1]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]
[2]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]

63
[ 5463-50-3 ]
3,6-dimethyl-2-(2,4,6-trimethyl-benzoyl)-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aluminium chloride 2: hydrogen chloride
	Multi-step reaction with 2 steps 1: aluminium chloride 2: diethyl ether
	Multi-step reaction with 2 steps 1: benzene; diethyl ether 2: hydrogen chloride

Multi-step reaction with 2 steps 1: benzene; diethyl ether 2: diethyl ether

64
[ 5463-50-3 ]
3-(2,4-dimethyl-phenyl)-3-methoxy-4,7-dimethyl-phthalide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: benzene; diethyl ether 2: thionyl chloride / Behandeln des Reaktionsprodukts mit Methanol und Pyridin
	Multi-step reaction with 2 steps 1: aluminium chloride 2: thionyl chloride / Behandeln des Reaktionsprodukts mit Methanol und Pyridin

Reference： [1]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]
[2]Newman; Lord [Journal of the American Chemical Society, 1944, vol. 66, p. 733]

65
[ 5463-50-3 ]
[ 69094-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: LiAlH₄ / diethyl ether 2: PBr₃ / diethyl ether; benzene 3: Na, AcOEt / diethyl ether

Reference： [1]Brickwood,D.J. et al. [Journal of the Chemical Society. Perkin transactions I, 1978, p. 1398 - 1414]

66
[ 5463-50-3 ]
[ 69094-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: LiAlH₄ / diethyl ether 2: PBr₃ / diethyl ether; benzene 3: Na, AcOEt / diethyl ether

Reference： [1]Brickwood,D.J. et al. [Journal of the Chemical Society. Perkin transactions I, 1978, p. 1398 - 1414]

67
[ 5463-50-3 ]
[ 50447-59-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: LiAlH₄ / diethyl ether 2: PBr₃ / diethyl ether; benzene 3: Na, AcOEt / diethyl ether

Reference： [1]Brickwood,D.J. et al. [Journal of the Chemical Society. Perkin transactions I, 1978, p. 1398 - 1414]

68
[ 5463-50-3 ]
[ 69094-44-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: LiAlH₄ / diethyl ether 2: PBr₃ / diethyl ether; benzene 3: Na, AcOEt / diethyl ether

Reference： [1]Brickwood,D.J. et al. [Journal of the Chemical Society. Perkin transactions I, 1978, p. 1398 - 1414]

69
[ 5463-50-3 ]
[ 50919-98-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (i) KOAc, (ii) NaOMe, MeOH, (iii) aq. HCl 2: HNO₃ / diethyl ether

Reference： [1]Buckle,D.R. et al. [Journal of Medicinal Chemistry, 1973, vol. 16, p. 1334 - 1339]

70
3-amino-piperidine-2,6-dione hydrogen chloride [ No CAS ]
[ 5463-50-3 ]
[ 244057-32-7 ]

Yield	Reaction Conditions	Operation in experiment
56%	With sodium acetate In acetic acid	5 2-(2,6-Dioxopiperidin-3-yl)-4,7-dimethylisoindoline-1,3-dione EXAMPLE 5 2-(2,6-Dioxopiperidin-3-yl)-4,7-dimethylisoindoline-1,3-dione 2-(2,6-Dioxopiperid-3-yl)-4,7-dimethylisoindoline-1,3-dione was prepared by the procedure of Example 1 from 3,6-dimethylphthalic anhydride (220 mg, 1.25 mmol), 3-aminopiperidine-2,6-dione hydrogen chloride (204 mg, 1.24 mmol) and sodium acetate (10 mg, 1.34 mmol) in acetic acid (10 mL). The product is a white solid (200 mg, 56% yield): mp 263.0-265.0° C.; 1H NMR (DMSO-d6) δ2.01-2.07 (m, 1H, CHH), 2.50-2.89 (m, 9H, CH3, CHH, CH2), 5.10 (dd, J=5.1, 12.4 Hz, 1H, NCH), 7.52 (s, 2H, Ar), 11.12 (br s, 1H, NH); 13C NMR (DMSO-d6) δ16.82, 22.02, 30.97, 48.59, 128.01, 135.04, 136.58, 167.68, 169.98, 172.83.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2001/6973, 2001, A1

71
[ 5463-50-3 ]
N-(t-butyloxycarbonylamino)-3,6-dimethylphthalimide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide	15.a 2-Amino-4,7-dimethylisoindoline (a) 52.9 g (0.3M) of 3,6-dimethylphthalic anhydride in 300 ml of N,N-dimethylformamide are heated to the boiling point over 15 minutes with 46.3 g (0.35M) of t-butylcarbazate. Subsequent to evaporation of the solvent, 64 g of N-(t-butyloxycarbonylamino)-3,6-dimethylphthalimide are obtained from ethanol. Mp. 187°-188° C. (Z).

Reference： [1]Current Patent Assignee: Beiersdorf (in: maxingvest); MAXINGVEST AG - US4526897, 1985, A

72
C₁₀H₁₀O₄ [ No CAS ]
[ 5463-50-3 ]

Yield	Reaction Conditions	Operation in experiment
43%	With sulfuric acid at -20 - 0℃;

Reference： [1]Kuck; Hackfort; Neumann; Stammler [Polish Journal of Chemistry, 2007, vol. 81, # 5-6, p. 875 - 892]

73
[ 5463-50-3 ]
[ 108-24-7 ]
[ 50920-06-4 ]

Yield	Reaction Conditions	Operation in experiment
39%	With potassium acetate at 100 - 155℃; for 6h;
36%	With potassium acetate at 100 - 155℃; for 8h;

Reference： [1]Kuck; Hackfort; Neumann; Stammler [Polish Journal of Chemistry, 2007, vol. 81, # 5-6, p. 875 - 892]
[2]Kirchwehm, Yvonne; Damme, Alexander; Kupfer, Thomas; Braunschweig, Holger; Krueger, Anke [Chemical Communications, 2012, vol. 48, # 10, p. 1502 - 1504]

74
[ 5463-50-3 ]
[ 63548-78-7 ]

Yield	Reaction Conditions	Operation in experiment
11%	at 820℃; Pyrolysis;

Reference： [1]Location in patent: experimental part Christoph, Hilmar; Grunenberg, Joerg; Hopf, Henning; Dix, Ina; Jones, Peter G.; Scholtissek, Martin; Maier, Guenther [Chemistry - A European Journal, 2008, vol. 14, # 18, p. 5604 - 5616]

75
[ 5463-50-3 ]
[ 1062569-46-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 20 h / Reflux 2: phosphorus tribromide / diethyl ether; benzene / 16.5 h / 20 °C 3: tetrabutylammomium bromide; rongalite / N,N-dimethyl-formamide / 19 h / 20 °C

Reference： [1]Kitamura, Chitoshi; Naito, Takao; Yoneda, Akio; Kawase, Takeshi; Komatsu, Toshiki [Chemistry Letters, 2010, vol. 39, # 7, p. 771 - 773]

76
[ 5463-50-3 ]
[ 1356835-89-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium proprionate / 20.5 h / 105 - 185 °C 2: toluene-4-sulfonic acid / benzene / 17 h / 110 °C / Molecular sieve