Name: 605-94-7|2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione|98%
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[ 605-94-7 ]
[ 3066-90-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium tetrahydroborate; In methanol; diethyl ether; water;	Step 1a: Synthesis of 2,3-Dimethoxy-5-methylhydroquinoneTo a stirred solution of NaBH4 (1.04 g, 27.5 mmol) in water (30 mL), a solution of commercial 2,3-dimethoxy-5-methylbenzoquinone (1.00 g, 5.50 mmol) in diethyl ether (15 mL) and methanol (8 mL) was added dropwise. Afterward, the reaction mixture was extracted with diethyl ether and washed with brine. The combined organic layers were dried over sodium sulphate and concentrated to dryness to give the product as a pale yellow solid (950 mg, 88%).TLC: R/= 0.20 petroleum ether:EtOAc 90:10 v/v. Spectroscopic data were as reported in the literature by Daquino, C. et al, J. Org. Chem. 2008, 75, 9270
		EXAMPLE 1Preparation of Grignard Reagent of 2,3 Dimethoxy-5-bromo-6-methyl 1,4 dimethoxyethoxy methyl ether Compound of Formula IIb2,3-Dimethoxy 5-methyl-1,4-benzoquinone of formula 2, (2.5 g) was dissolved in 7.5 ml of methylene dichloride and treated with sodium hydrosulphite (3.56 g) in an alkaline solution at 10-20 C. After 2 hours the reaction mixture was treated with conc. HCl (3.4 ml) to acidic pH. The reaction mixture was extracted with methylene dichloride and washed with water. The organic solvent was concentrated and poured in hexane. The precipitated solid was filtered to obtain 2.25 g of 2,3-dimethoxy-5-methyl-1,4-hydroquinone compound of formula 4. The solid was taken in methylene dichloride and treated with bromine (1.96 g) at 10 to 20 C. The reaction was quenched in water after 2 hours and extracted in methylene dichloride. The methylene dichloride was evaporated. The concentrated mass was added to hexane to precipitate out the solid of 2,3-dimethoxy-5-bromo-6-methyl-1,4-hydroquinone (3.06 g). The bromo compound was dissolved in toluene and treated with 1.024 g sodium hydride (60% suspension) in toluene at 0 to -5 C. Methoxyethoxy methyl chloride (3.17 g) was added at 5 to 10 C. The temperature was slowly raised to room temperature and the reaction was continued for 2 hrs. The reaction was quenched with methanol, followed by water and the toluene layer separated. The organic layer was distilled under vacuum to obtain 4.65 g of 2,3-dimethoxy-5-bromo-6-methyl-1,4-hydroquinone dimethoxyethoxy methyl ether compound of the formula 14a. The compound of formula 14a (4.65 g) was reacted with Magnesium (0.301 g) in tetrahydrofuran, in presence of a pinch of iodine at ambient temperature to form the Grignard reagent of 2,3 dimethoxy-5-bromo-6-methyl 1,4 dimethoxyethoxy methyl ether compound of formula IIb; EXAMPLE 2Preparation of Grignard Reagent of 2,3 Dimethoxy-5-bromo-6-methyl 1,4 dimethoxyethoxy methyl ether Compound of Formula IIb 2,3 dimethoxy 5-methyl 1,4 benzoquinone compound of formula 2 (2.5 g) was dissolved in 7.5 ml of methylene dichloride and treated with sodium hydrosulphite (3.56 g) in alkaline solution at 10-20 C. After 2 hours the reaction mixture was treated with conc. HCl 3.4 ml to acidic pH. The reaction mixture was extracted with methylene dichloride and washed with water. The organic solvent was concentrated and poured in hexane (10 ml). The precipitated solid was filtered to obtain 2.25 g of 2,3 dimethoxy 5 methyl 1,4 hydroquinone compound of formula 4. The solid was taken in methylene dichloride 15 ml and treated with bromine (1.96 g) at 10-20 C. The reaction was quenched in water after 2 hours and extracted in methylene dichloride. The methylene dichloride was evaporated. The concentrated mass was added to hexane to precipitate out the solid of 2,3 dimethoxy-5 bromo-6-methyl 1,4 hydroquinone (3.06 g). The bromo compound was dissolved in methanol and treated with sodium methoxide (1.5 g) at 5-10 C. Methoxyethoxy methyl chloride (3.17 g) was added at 5 C.-10 C., the temperature raised to room temperature and maintained for 8 hrs. The reaction was quenched in water and extracted in diisopropyl ether. The organic layer was distilled under vacuum to obtain 4.75 g of 2,3 Dimethoxy-5-bromo-6-methyl 1,4 di methoxyethoxy methyl ether compound of the formula 14a. The compound was reacted with magnesium (0.34 g) in tetrahydrofuran, in presence of a pinch of iodine at ambient temperature to form the Grignard reagent of 2,3 dimethoxy-5-bromo-6-methyl 1,4 dimethoxyethoxy methyl ether of the formula IIb.; EXAMPLE 3Preparation of Grignard Reagent of 2,3,4,5 tetramethoxy-6-methyl-bromobenzene Compound of Formula IIc 2,3dimethoxy-5-methyl 1,4 benzoquinone compound of formula 2, 2.5 g was dissolved in 7.5 ml of methylene dichloride and treated with sodium hydrosulphite (3.56 g) in alkaline solution at 10-20 C. After 2 hours the reaction mixture was treated with conc. HCl (3.4 ml) to acidic pH. The reaction mixture was extracted with methylene dichloride and washed with water. The organic solvent was concentrated and poured in hexane. The precipitated solid was filtered to obtain 2.25 g. of 2,3 dimethoxy 5 methyl 1,4 hydroquinone compound of formula 4. The solid was taken in alkaline solution and dimethyl sulphate (5.75 g) was added at 40-50 C. The reaction mixture was quenched after 4 hours in water and extracted in methylene dichloride. The solvent was evaporated and the crude obtained was distilled under vacuum at 80 C. at 0.5-1.0 mm Hg to obtain 2.33 g of 2,3,4,5-tetramethoxy toluene. The compound was taken in methylene dichloride (15 ml) and treated with bromine (1.75 g) at 10-20 C. The reaction was quenched in water after 2 hours and extracted in methylene dichloride. The methylene dichloride was evaporated. The concentrated mass was added to hexane to precipitate out the solid of 2,3,4,5-tetramethoxy-6-methyl bromobenzene (3.03 g) of formula 14b. The compound of formula 14b was reacted wit...
	With potassium borohydride; In methanol; at 0℃; for 0.166667h;	To a solution of coenzyme Q0 1 (4.00 g, 21.7 mmol) in methanol (30 mL) at 0 C was dropwise added a solution of KBH4 (5.85 g, 108.5 mmol) in methanol (30 mL). After 10 min, the reaction was quenched by the addition of EtOAc and then 5% aqueous HCl[38] and [39] (see Scheme 4). The mixture was extracted with EtOAc (3×50 mL) and the organic layer was washed successively with water and brine, dried (MgSO4), and evaporated at reduced pressure. The crude hydroquinone (4.20 g) was dissolved in EtOH (20 mL) and to this solution at room temperature was added a solution of NaOH (2.20 g in 6 mL H2O) and dimethyl sulfate (5.30 mL, 56.0 mmol) with cooling in a ice water bath in six portions simultaneously. After 45 min, 5% aqueous HCl was added and the mixture was extracted with EtOAc (3×50 mL). The organic layer was washed successively with water and brine, dried (MgSO4), and evaporated to give 5a (74%) as a light yellow liquid.40 1H NMR (500.0 MHz, CDCl3, 298 K): 3.99 (s, 12H, 4× -OCH3), 2.25 (s, 3H, -CH3), 6.45(s, 1H, ArH) ppm.

	With sodium tetrahydroborate; In methanol; diethyl ether; water; at 20℃; for 4.5h;	5.29 g [140 mmole] of sodium borohydride was weighed into a 500 mL round bottom flask fitted with an addition funnel and stir bar. Added 150 mL of water. Charged 5.03 g [27.6 mmole] of 2,3-dimethoxy-5-methyl-p-benzoquinone dissolved in a mixture of 75 mL Et20 and 35 mL MeOH into the addition funnel. Started the stirrer in the reaction flask and added the red solution of quinone dropwise over 90 minutes under ambient conditions. The red droplets changed color to yellow upon entering the reaction mixture and there was a mild exotherm with gas evolution. After addition was complete, the two phase yellow solution was stirred at room temperature for 3 h. Quenched the reaction to pH --2 with conc. HC1. Extracted the reaction mixture with 3 x 150 mL MTBE. Washed the combined organic phases with 150 mL of 1.0 M pH 5.5 phosphate buffer, 150 mL of brine, and dried over Mg504. Added 50 mL heptane to chase out low boiling solvents and water and removed the solvent on rotavap to 500/10 Toff to obtain 5.43 g of the crude product (1) as an amber oil. The crude material was used without further purification.
	With sodium tetrahydroborate; In methanol; Et2O; water; at 20℃; for 0.25h;	Example 14 Synthesis of (S)-5,6-bis(nitrooxy)hexyl 3-(4,5-dimethoxy-2-methyl-3,6- dioxocyclohexa-l,4-dienyl)-3-methylbutanoate (Compound 17; (S)-isomer of compound 11) Step 1 : Synthesis of 2, 3- ene-l,4-diol NaBH4 (5.2g; 137.2 mmol) was dissolved in 150 ml of water, and a solution of 2,3-dimethoxy-5-methylcyclohexa-2,5-diene-l,4-dione (Sg; 27.4 mmol) in a mixture of 75 ml of Et20 and 38 ml of MeOH was added at room temperature with stirring. After 15 min, the mixture was placed in a separatory funnel, and the layers were allowed to separate. The ether phase was removed and the aqueous phase was extracted twice with 50 ml portions of ether. The combined organic extracts were washed with brine and dried over Na2S04. Solvent removal under reduced pressure afforded the title compound (9 g; 88%) as red oil. It was used in the next step without further purification.
	With sodium tetrahydroborate; In methanol; water; at 20℃;	Example 15 Synthesis of (S)-5,6-bis(nitrooxy)hexyl 3-(4,5-dimethoxy-2-methyl-3,6- dioxocyclohexa-l,4-dienyl)-3-methylbutanoate (Compound 17; (S)-isomer of compound 11) Step 1 : Synthesis of 2, 3- ene-l,4-diol NaBH4 (5.2g; 137.2mmol) was dissolved in 150 ml of water, and a solution of 2,3-dimethoxy-5-methylcyclohexa-2,5-diene-l,4-dione (Sg; 27.4mmol) in a mixture of 75 ml of Et20 and 38 ml of MeOH was added at room temperature with stirring. After 15 min, the mixture was placed in a separatory funnel, and the layers were allowed to separate. The ether phase was removed and the aqueous phase was extracted twice with 50 ml portions of ether. The combined organic extracts were washed with brine and dried over Na2S04. Solvent removal under reduced pressure afforded the title compound (9g; 88%) as red oil. It was used in the next step without further purification.

Reference： [1]Helvetica Chimica Acta,2005,vol. 88,p. 2575 - 2581
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[3]Journal of Organic Chemistry,1989,vol. 54,p. 3303 - 3310
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[5]Patent: WO2015/155234,2015,A1 .Location in patent: Page/Page column 39; 40
[6]Journal of Organic Chemistry,2019,vol. 84,p. 13655 - 13664
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[12]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 3182 - 3186
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    Angew. Chem.,2017,vol. 129,p. 8308 - 8312,5

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[ 605-94-7 ]
[ 2885-00-9 ]
[ 53092-26-5 ]

Reference： [1]Journal of Medicinal Chemistry,1974,vol. 17,p. 893 - 896

3
[ 6443-69-2 ]
[ 605-94-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With dihydrogen peroxide; In formic acid; water; acetic acid; at 35℃; for 2h;	3,4,5-Trimethoxytoluene (1, 3.6 g, 0.02 mol) was dissolved in a mixture of HCO2H (5 mL) and AcOH (2.5 mL); 30% H2O2 solution(9 mL, 0.08 mol) was added dropwise over 10 min. The mixture was stirred and heated at 35 C for 2 h and diluted with H2O and extracted with CH2Cl2 (3 × 30 mL). The combined organic phases were washed with H2O until pH 7, then dried (anhyd Na2SO4), and evaporated under reduced pressure. The residue was purified by column chromatograph (silica gel, petroleum ether-EtOAc, 5:1) to give coenzymeQ0 (3.1 g, 86% isolated yield) as red-colored needles; mp55-58 C (Lit.10 57-59 C).1H NMR (500 MHz, CDCl3): delta = 6.42 (s, 1 H), 4.00 (s, 3 H), 3.98(s, 3 H), 2.02 (s, 3 H).MS (ESI): m/z =183 (M+ + H).
86%	With peracetic acid; sulfuric acid; In ethanol; at 35℃; for 2h;	3 g of 3,4,5-trimethoxytoluene was weighed and 0.33 ml of concentrated sulfuric acid was added to 10 ml of an ethanol solution. After stirring and stirring, the mixture is slowly added dropwise to a concentration of 10 mol/L oxidant peroxyacetic acid 4 ml, 10 minutes after the drop the reaction was stopped at 35 C for 2 hours. TLC point plate monitoring of raw materials have been all finished, stop the reaction, add water 20ml The reaction was quenched with dichloromethane and the organic layer was washed three times with 5% FeCh 30 mL and washed with water until the pH was 6. After the organic layer was combined and dried, the red needle-like crystal coenzyme Qo was recrystallized from petroleum ether, the yield was 86%
85%	With dipotassium peroxodisulfate; sulfuric acid; acetic acid; at 50℃; for 1h;	3,4,5-Trimethoxytoluene (1.82 g, 10 mmol) was dissolvedin a mixture of acetic acid (10 mL) and catalytic H2SO4 (0.01 mL), then a solution of the oxidant (15 mmol) was added dropwise over 10 min. The mixture was stirred and heated at 50C for 1 h. After cooling, the reaction mixture was extracted with CH2Cl2 (3 × 10 mL). The combined organic phases were washed with H2O and NaHCO3, then dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (PE/EtOAc, 5:1) to give CoQ0. CoQ0, red-colored needles, m.p. 55C-58C (Lit.1357C-59C).1H NMR (400 MHz, CDCl3): delta = 6.44 (q, J = 1.7 Hz, 1H),4.02 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 2.04 (d, J = 1.6 Hz,3H, CH3).13C NMR (101 MHz, CDCl3): delta = 184.4 (C=O), 184.2(C=O), 145.0, 144.8, 144.0, 131.2, 61.2 (OCH3), 61.1(OCH3), 15.4 (CH3).MS (ESI): m/z = 205 [M + Na]+.The spectroscopic data are in accord with the literature.

52%	With 2-Iodobenzoic acid; oxone\|\|potassium monopersulfate triple salt; In water; acetonitrile; at 20℃; for 1h;	General procedure: To a suspension of anisole derivative (1.0 mmol), 2-IB (1.0 mmol,248 mg), and Oxone (3.0 mmol, 1.844 g) in MeCN (4 mL) was added water (6 mL). The mixture was stirred at room temperature until complete consumption of the starting material (confirmed by TLCanalysis). Then, the insoluble material was removed by filtration with CH2Cl2 and then the organic layer was extracted with CH2Cl2 (50 mL) at twice. The extract was washed with a saturated NaHCO3 aqueous solution(100 mL) and then filtered through filter paper for dehydration. After the solvent was removed by evaporation, the desired product was purified by flash silica gel chromatography with appropriate solvent.
5 - 88%		To a round-bottom flask (20 mL) equipped with a reflux condenser was added a solution of commercial 3,4,5-trimethoxy-toluene (0.547 g, 3 mmol) in AcOH (3 mL), followed by para-toluenesulfonic acid monohydrate (57 mg, 0.3 mmol) as catalyst. The oxidant H2O2 (30%, 0.65 mL, 6 mmol) was then added. The reaction mixture was stirred and heated at 75 C. for 30 min. The resulting dark-red solution was cooled to 0-5 C., and concentrated HNO3 (90%, 1.5 mmol) was then slowly added. The cold solution was poured into H2O (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with H2O (80 mL) in order to remove traces of AcOH, dried (Na2SO4) and filtered. When the solvent was evaporated under vacuum, the final crude (0.528 g, dark-red oil) was dissolved in boiling hexane (70 mL), filtered, and the solvent was removed to give the pure 2,3-Dimethoxy-5 methyl-[1,4]benzoquinone (0.480 g, 88% yield) as red needles. 1H NMR (400 MHz, CDCl3, ppm): delta2.04 [d, 3H, J=1.6 Hz, CH3], 4.00 [s, 3H, OCH3], 4.02 [s, 3H, OCH3], 6.43-6.44 [q, 1H, Jm=1.6 Hz]. 13C NMR (400 MHz, CDCl3, ppm): delta15.4, 31.1, 61.2, 131.3, 144.0, 144.9, 145.1, 184.1, 184.4. MS m/z (%): 182 (85), 167 (32), 153 (13), 137 (100), 121 (6), 111(23), 96 (12), 83 (67), 69 (31), 53 (15).; Example 5; Continuous Synthesis of 2,3-Dimethoxy-5-methyl-[1,4]benzoquinone [CoQ0]; The continuous synthesis took place in a continuous flow reactor as described below, and the retention time was only 30 minutes.The 3,4,5-trimethoxy toluene (18.2 g, MW 182.21, 0.1 mol), the PTS acid (1.7 g, MW 172.13, 0.01 mol) are dissolved in glacial acetic acid to give a total volume of 50 ml and the solution is connected to the pump 1. The hydrogen peroxide (0.2 mol, MW 34.02, 21.6 ml if H2O2 at 30% and 17.5 ml if H2O2 at 35%) diluted to 50 ml with glacial acetic acid is connected to the pump 2. The nitric acid (90%, 0.05 mol, MW 63.02, d 1.49, 3.15 g, 3.5 g solution 90%, 2.35 ml solution 90%) dissolved in acetic acid (to 50 ml) is connected to the pump 3. Pumps 1, 2, 3 were working respectively at 4.95, 4.95, and 9.45 rpm corresponding about at 0.63 ml/min. Isoversinic tubes used had an ID 1 mm. The residence time of the reaction was about 30 min (38 ml volume reactor) and the reaction was performed at 750 C. pumping the solutions of the pumps 1 and 2. After 30 min the nitric acid solution was pumped into the second section of the reactor (11 ml, volume reactor) refrigerated with water system.The reaction mixture is poured in water (about 100 ml) as soon as is out of the reactor. The colour is intense red. It was necessary to add about 6.5 ml of H2O2 solution as above prepared due to the final different consume speed of the reagents. About 50 ml of glacial acetic acid was also pumped in the reactor at the end in order to push out all of the reaction solution.Work-up: The mixture is evaporated at the rotavapor in order to reduce the total volume. 300 ml of water (and 3 g of NaCl) were added and the mixture was extracted with CH2Cl2 (4×100 ml), dried and the solvent evaporated obtaining a red oil. The red oil was suspended in 400 ml boiling hexane. The soluble phase is separated from the red-black gummy and evaporated under reduced pressure to give 10.7 g of red oil. The yield was 5%.; Example 6-Example 5; Continuous Synthesis of 2,3-Dimethoxy-5-methyl-[1,4]benzoquinone [CoQ0]; The continuous synthesis took place in a continuous flow reactor as described below, and the retention time was only 5 minutes.3,4,5-Trimethoxy toluene (18.2 g, MW 182.21, 0.1 mol), para-toluene sulphonic acid (1.7 g, MW 172.13, 0.01 mol) are dissolved in glacial acetic acid to give a total volume of 50 ml and the solution is connected to the pump 1. Hydrogen peroxide (0.2 mol, MW 34.02, 21.6 ml if H2O2 at 30% and 17.5 ml if H2O2 at 35%) diluted to 50 ml with glacial acetic acid is connected to the pump 1 (second tube). The nitric acid (90%, 0.05 mol, MW 63.02, d 1.49, 3.15 g, 3.5 g solution 90%, 2.35 ml solution 90%) dissolved in acetic acid (to 50 ml) is connected to the pump 2. The pump 1 is pumping approximately 3.8 ml/min for each of the two reagent solutions (total speed flow 7.6 ml/min, i.e. 38 ml reactor volume/5 min RT). Isoversinic tubes (ID 2 mm) was used on the peristaltic pump. The residence time of the reaction was about 5 min (38 ml volume reactor) and the reaction was performed at 75 C. pumping the solutions of the pumps 1. After 5 min the nitric acid solution was pumped at 3.8 ml/min into the second section of the reactor (11 ml, volume reactor) cooled by a cold water circuit.About 50 ml of glacial acetic acid was also pumped in the reactor at the end in order to push out all of the reaction solution.Work-up: similar as in example 5. The yield was 20%.
	With dihydrogen peroxide; In formic acid; water; at 40 - 50℃; for 1h;	Example 3 - Oxidation; A 4 liter reactor, equipped with a mechanical stirrer, was filled with trimethoxytoluene (100 g, 0.54 mol), formic acid (550 g) and water (450 g). After heating to 400C, aq. H2O2 (30%, 318g, 2,79 mol) was slowly added, controlling the temperature between 40 and 5O0C. After the addition, the reaction was stirred at 400C for 1 hour. The mixture is extracted twice with dichloromethane (800 g each). The combined organic phases are washed with water (500 g), dried over MgSO4, filtered, evaporated and dried under vacuum, yielding a red oil (40 g) containing the desired 2,3-dimethoxy-6-methyl-1 ,4- benzoquinone as the mayor component).

Reference： [1]Organic process research and development,2010,vol. 14,p. 1379 - 1384
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[3]Patent: CN107011146,2017,A .Location in patent: Paragraph 0020; 0023; 0025; 0027; 0029; 0031; 0033
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[10]Journal of Organic Chemistry,1987,vol. 52,p. 3872 - 3875
[11]Patent: US2008/287702,2008,A1 .Location in patent: Page/Page column 3; 4-5
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[19]Patent: WO2006/32425,2006,A2 .Location in patent: Page/Page column 10
[20]Organic Preparations and Procedures International,2019,vol. 51,p. 602 - 605

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[ 6443-69-2 ]
[ 605-94-7 ]
[ 39068-88-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	With perchloric acid; dihydrogen peroxide In acetonitrile at 60℃; for 1h;
1: 21% 2: 18%	With sulfuric acid; 3,3-dimethyldioxirane In acetone at 20℃; for 2h;

Reference： [1]Zalomaeva, Olga V.; Evtushok, Vasilii Yu.; Maksimov, Gennadii M.; Maksimovskaya, Raisa I.; Kholdeeva, Oxana A. [Dalton Transactions, 2017, vol. 46, # 16, p. 5202 - 5209]
[2]Adam; Shimizu [Synthesis, 1994, # 6, p. 560 - 562]

6
[ 494-99-5 ]
[ 605-94-7 ]
[ 614-13-1 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 1652 - 1657
[2]Journal of Organic Chemistry,1988,vol. 53,p. 5453 - 5457

7
[ 35896-58-3 ]
[ 605-94-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With dipotassium peroxodisulfate; In water; at 25℃; for 1h;	Compound 3 (0.32 g, 1.5 mmol) was dissolved in acetonitrile (2 mL), and an excess of asolution of K2S2O8 (1.6 g, 6 mmol) in 3mL water was added at 25 C. The reactionmixture was stirred at room temperature for 1 h. The progress of the reaction was monitoredby TLC. After completion of the reaction, the mixture was extracted withdichloromethane (10mL 3). The organic layers were washed with brine until neutrality,then dried over anhydrous Na2SO4 and concentrated in vacuo. The crude productwas purified by a silica-gel column chromatography with petroleum ether and EtOAc(3:1) to give CoQ0, 0.26 g, 96%, red needles, m.p 56-57 C (lit5 57-59 C). IR: (cm1)3590, 3415, 1661, 1603, 1291, 1226, 999. 1H NMR (400 MHz, CDCl3) d 6.44 (q,J1.7 Hz, 1H), 4.02 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 2.04 (d, J1.6 Hz, 3H,CH3). 13C NMR (101 MHz, CDCl3) d 184.4 (C5O), 184.2(C5O), 145.0, 144.8, 144.0,131.2, 61.2 (OCH3), 61.1 (OCH3), 15.4 (CH3). GC-MS (EI): m/z 182. The spectroscopicdata are in accord with the literature
	With ammonium cerium (IV) nitrate; In tetrahydrofuran; water; at 0 - 25℃; for 2h;	General procedure: A solution of compounds 1, 4, 5 (2.5 mmol) in THF (10 mL) was diluted with water (5 mL), and an excess solution of cerricammonium nitrate (CAN) (3.9 g, 7 mmol) in 10 mL water was added at 0 C. The mixture was stirred at room temperature for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the THF was removed under a vacuum at 40 C, and the crude mixture was extracted with three portions of CH2Cl2 (20 mL). The orange extracts were washed with brine until neutrality, then dried over anhydrous Na2SO4 and concentrated in vacuo. The crude products were purified by a silica-gel column chromatography with petroleum ether and EtOAc as eluent to give the desired benzoquinones 2, 7, 6.

Reference： [1]Organic Preparations and Procedures International,2019,vol. 51,p. 602 - 605
[2]Journal of Organic Chemistry,1987,vol. 52,p. 3872 - 3875
[3]European Journal of Medicinal Chemistry,2014,vol. 86,p. 710 - 713

8
[ 605-94-7 ]
[ 30685-17-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With bromine; In tetrachloromethane; at 20℃; for 4h;	To a stirred solution of coenzyme Q0 1 (10.60 g, 58.0 mmol) in 120 mL of carbon tetrachloride was added dropwisely bromine (10.52 g, 68.0 mmol) at room temperature21 S. Kikumasa, I. Seiichi and Y. Ryohei, J. Org. Chem. 37 (1972), p. 1889.21 (see Scheme 2). The reaction mixture was stirred for 4 h, and then treated with water, dried with magnesium sulfate, and evaporated. The reaction mixture was purified by column chromatography to give 2 (81%) as red needle crystals. 1H NMR (500.0 MHz, CDCl3, 298 K): 3.95 (s, 3H, -OCH3), 4.05 (s, 3H, -OCH3), 2.22 (s, 3H, -CH3) ppm.
81%	With bromine; In tetrachloromethane; at 20℃; for 12h;	To a solution of the 2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (1.82, 10 mmol) in CCl4 (40 mL) was added Br2 (0.68g, 15mmol) at room temperature. The resulting solution was stirred at ambient temperature for 12 h, then concentrated in vacuo, The crude residue was purified by column chromatography on silica gel (EtOAc-petroleum ether = 1:25) to yield the title compound (2.1 g, yield : 81 %) as a brick-red solid. 1H NMR (400 MHz, CDCl3) delta 4.05 (s, 3H), 4.02 (s, 3H), 2.23 (s, 3H). MS (ESI): m/z 262.0 [M+H]+

Reference： [1]Tetrahedron,2011,vol. 67,p. 5990 - 6000
[2]Bioorganic Chemistry,2019,vol. 89
[3]Chemical Communications,2013,vol. 49,p. 1738 - 1740
[4]Journal of Organic Chemistry,1972,vol. 37,p. 1889 - 1892
[5]Chemical Science,2017,vol. 8,p. 6474 - 6483

9
[ 605-94-7 ]
[ 7541-49-3 ]
[ 51077-59-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1965,vol. 13,p. 130 - 135

10
[ 605-94-7 ]
[ 32529-79-6 ]
[ 143914-76-5 ]
[ 143914-75-4 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 8666 - 8680

11
[ 605-94-7 ]
[ 542-92-7 ]
[ 152984-32-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With acetic acid; at 20℃;	To a solution of 2,3-dimethoxy-5-methyl-p-benzoquinone (4.0 g, 21.96 mmol) in glacial acetic acid (100 mL) was added freshly distilled cyclopentadiene (2.8 mL, 32.94 mmol, 1.5 eq) and the reaction was stirred overnight at r.t. The reaction was cooled to 0C and ice/water was added. The aqueous layer was neutralized using 3M aq NaOH and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with water, brine, dried on Na2SO4, filtered and evaporated affording the title compound (5.4 g, yield: 98%) as a dark red oil. 1H NMR (300 MHz, CDC13) delta 6.16 (dd, J = 5.6, 2.9, 1H), 6.01 (dd, J = 5.6, 2.8, 1H), 3.94 (s, 3H), 3.92 (s, 3H), 3.42 (s, 1H), 3.08 (s, 1H), 2.83 (d, J = 3.9, 1H), 2.07 (d, J = 12.6, 3H), 1.71 - 1.62 (m, 1H), 1.54 (dt, J = 9.2, 1.6, 1H).
98%	With acetic acid; at 20℃;	Step 1: Synthesis of 4,5-dimethoxy-2-methyltricyclo[6.2.1.02,7] undeca- 4,9-diene-3,6-dione To a solution of 2,3-dimethoxy-5-methyl-p-benzoquinone (4.0 g, 21.96 mmol) in glacial acetic acid (100 mL) was added freshly distilled cyclopentadiene (2.8 mL, 32.94 mmol, 1.5 eq) and the reaction was stirred overnight at r.t. The reaction was cooled to 0C and ice/water was added. The aqueous layer was neutralized using 3M aq NaOH and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with water, brine, dried on Na2SO4, filtered and evaporated affording the title compound (5.4 g, yield: 98%) as a dark red oil. 1H NMR (300 MHz, CDC13) delta 6.16 (dd, J = 5.6, 2.9, 1H), 6.01 (dd, J = 5.6, 2.8, 1H), 3.94 (s, 3H), 3.92 (s, 3H), 3.42 (s, 1H), 3.08 (s, 1H), 2.83 (d, J= 3.9, 1H), 2.07 (d, J= 12.6, 3H), 1.71 - 1.62 (m, 1H), 1.54 (dt, J= 9.2, 1.6, 1H).
98%	In acetic acid; at 20℃;	Step lb: Synthesis of 4,5-dimethoxy-2-methyltricyclo[6.2.1.02,7] undeca-4,9- diene-3,6-dioneTo a solution of 2,3-dimethoxy-5-methyl-p-benzoquinone (4.0 g, 21.96 mmol) in glacial acetic acid (100 mL), freshly distilled cyclopentadiene (2.8 mL, 32.94 mmol, 1.5 eq) was added and the reaction was stirred overnight at r.t. The reaction was cooled to 0C and ice/water was added. The aqueous layer was neutralized using 3M aq NaOH and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with water, brine, dried on Na2S04, filtered and evaporated affording the title compound (5.4 g, yield: 98%) as a dark red oil.1H NMR (300 MHz, CDC13) delta 6.16 (dd, J= 5.6, 2.9, 1H), 6.01 (dd, J= 5.6, 2.8,1H), 3.94 (s, 3H), 3.92 (s, 3H), 3.42 (s, 1H), 3.08 (s, 1H), 2.83 (d, J= 3.9, 1H), 2.07 (d, J = 12.6, 3H), 1.71 - 1.62 (m, 1H), 1.54 (dt, J= 9.2, 1.6, 1H).

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 1657 - 1664
[2]Organic Preparations and Procedures International,2004,vol. 36,p. 476 - 479
[3]Patent: WO2013/60673,2013,A1 .Location in patent: Page/Page column 49
[4]Patent: WO2014/63923,2014,A1 .Location in patent: Page/Page column 45-46
[5]Patent: WO2015/155234,2015,A1 .Location in patent: Page/Page column 42
[6]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 6429 - 6441
[7]Synthetic Communications,2004,vol. 34,p. 4049 - 4053

12
[ 494-99-5 ]
[ 937-14-4 ]
[ 605-94-7 ]
[ 4502-01-6 ]
[ 61413-56-7 ]
3-Chloro-benzoic acid (1S,6R)-6-hydroxy-3-methoxy-6-methyl-2,5-dioxo-cyclohex-3-enyl ester [ No CAS ]
[ 614-13-1 ]

Reference： [1]Heterocycles,1998,vol. 47,p. 647 - 650

13
[ 605-94-7 ]
[ 68799-83-7 ]
[ 303-98-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (all-E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl bromide With tri-n-butyl-tin hydride; lithium diisopropyl amide In tetrahydrofuran; hexane for 2h; Stage #2: 2,3-Dimethoxy-5-methyl-1,4-benzoquinone With silver(l) oxide In dichloromethane for 2h; Further stages.;

Reference： [1]Boers, Rutger B.; Gast, Peter; Hoff, Arnold J.; De Groot, Huub J. M.; Lugtenburg, Johan [European Journal of Organic Chemistry, 2002, # 1, p. 189 - 202]

14
[ 22383-85-3 ]
[ 605-94-7 ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 4049 - 4053

15
[ 605-94-7 ]
[ 35896-58-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2371 - 2375
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1125 - 1129
[3]Journal of the American Chemical Society,1999,vol. 121,p. 11664 - 11673
[4]Tetrahedron,1998,vol. 54,p. 1241 - 1253
[5]Tetrahedron,1996,vol. 52,p. 7265 - 7276
[6]Tetrahedron,2011,vol. 67,p. 5990 - 6000
[7]Journal of the American Chemical Society,2011,vol. 133,p. 12366 - 12369
[8]Chemistry - An Asian Journal,2011,vol. 6,p. 1064 - 1073

16
[ 605-94-7 ]
[ 73875-27-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SnCl₂; aq. HCl / ethanol 2: 990 mg / aq. KOH / 1 h / 80 °C 3: 84 percent / Br₂ / CH₂Cl₂ / 0.08 h / 3 - 5 °C
	Multi-step reaction with 3 steps 1: H₂ / Pd/C / methanol / 1551.44 - 2327.17 Torr 2: NaOH / methanol 3: NBS / CH₂Cl₂

Reference： [1]Daines, Alison M.; Abell, Andrew D. [Organic and Biomolecular Chemistry, 2004, vol. 2, # 16, p. 2371 - 2375]
[2]Jung, Young-Sik; Joe, Bo-Young; Cho, Sung Ju; Konishi, Yasuo [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 4, p. 1125 - 1129]

17
[ 605-94-7 ]
[ 303-98-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 97 percent / aq. Na₂S₂O₄ / 1,2-dichloro-ethane / 3 h / 20 °C 2.1: 84.1 percent / Na / ethanol / 3 h / -20 °C 3.1: BuLi; N,N,N',N'-tetramethylethylenediamine / hexane / 1 h / 0 °C 3.2: 59.6 percent / hexane; tetrahydrofuran / 3.5 h / -40 - 20 °C 4.1: (COCl)2; DMSO / CH₂Cl₂ / 1 h / -60 - -40 °C 4.2: 94.9 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C 5.1: 91.7 percent / CH₂Cl₂ / 4 h / Heating 6.1: 87.3 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating 7.1: Et₃N; MsCl / CH₂Cl₂ / 1.5 h / -40 °C 7.2: 95.5 percent / LiBr / tetrahydrofuran; CH₂Cl₂ / 2.5 h / 0 °C 8.1: BuLi; HMPA / tetrahydrofuran; hexane / 1 h / -70 °C 8.2: 85.3 percent / tetrahydrofuran; hexane / 2 h / -70 - 0 °C 9.1: 99.8 percent / sodium naphthalenide / tetrahydrofuran / 1 h / -78 °C 10.1: 93 percent / aq. HCl; air / methanol; hexane / 4 h / 40 °C
	Multi-step reaction with 7 steps 3: 77 percent / CuCl / tetrahydrofuran / -50 °C 4: 89 percent / BuLi, p-Me-C₆H₄-SO₂Cl, LiBr 6: Na, EtOH / tetrahydrofuran / Ambient temperature 7: 1.) H(+), 2.) air

Reference： [1]Yu, Xiong-Jie; Chen, Fen-Er; Dai, Hui-Fang; Chen, Xu-Xiang; Kuang, Yun-Yan; Xie, Bin [Helvetica Chimica Acta, 2005, vol. 88, # 10, p. 2575 - 2581]
[2]Sato, Kikumasa; Miyamoto, Osamu; Inoue, Seiichi; Yamamoto, Tomoya; Hirasawa, Yukihiko [Journal of the Chemical Society. Chemical communications, 1982, # 3, p. 153 - 154]

18
[ 20734-74-1 ]
[ 605-94-7 ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 189 - 202

19
[ 1916-07-0 ]
[ 605-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 86.4 percent / 99 percent N₂H₄*H₂O / methanol / 5 h / Heating 2: 85 percent / K₃Fe(CN)6; 25 percent NH₄OH / H₂O; CH₂Cl₂ / 4 h / 20 °C 3: 65 percent / Zn-Hg / acetic acid; toluene; H₂O / 0.75 h / Heating 4: 80 percent / 50 percent H₂O₂; 98 percent HCOOH; phosphomolybdic acid / 0.25 h / 20 °C
	Multi-step reaction with 3 steps 1: LiAlH₄ / tetrahydrofuran 2: H₂ / Pd-C / acetic acid / 2206.5 Torr / Ambient temperature 3: aq. H₂O₂, AcOH
	Multi-step reaction with 4 steps 1: LiAlH₄ / tetrahydrofuran 2: H₂ / Pd-C / acetic acid / 2206.5 Torr / Ambient temperature 3: aq. H₂O₂, AcOH, H₂SO₄ 4: aq. H₂O₂, AcOH, H₂SO₄

	Multi-step reaction with 2 steps 1: (i) LiAlH₄, THF, (ii) /BRN= 635994/, aq. NaOH 2: aq. H₂O₂, AcOH
	Multi-step reaction with 3 steps 1: (i) LiAlH₄, THF, (ii) /BRN= 635994/, aq. NaOH 2: aq. H₂O₂, AcOH, H₂SO₄ 3: aq. H₂O₂, AcOH, H₂SO₄

Reference： [1]Chida; Vani; Chandrasekharam; Srinivasan; Singh [Synthetic Communications, 2001, vol. 31, # 5, p. 657 - 660]
[2]Sugihara; Watanabe; Kawamatsu; Morimoto [Justus Liebigs Annalen der Chemie, 1972, vol. 763, p. 109 - 120]
[3]Sugihara; Watanabe; Kawamatsu; Morimoto [Justus Liebigs Annalen der Chemie, 1972, vol. 763, p. 109 - 120]
[4]Sugihara; Watanabe; Kawamatsu; Morimoto [Justus Liebigs Annalen der Chemie, 1972, vol. 763, p. 109 - 120]
[5]Sugihara; Watanabe; Kawamatsu; Morimoto [Justus Liebigs Annalen der Chemie, 1972, vol. 763, p. 109 - 120]

20
[ 19676-64-3 ]
[ 605-94-7 ]

Reference： [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 1648 - 1650
[2]Bulletin of the Chemical Society of Japan,1972,vol. 45,p. 3455 - 3457

21
[ 36776-51-9 ]
[ 605-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaOMe, CuCN / 1.) methanol, DME, dimethyl carbonate, 80 deg C, 5 h 2.) methanol, DME, water, RT, 2 h 2: 84 percent / pyridine-2,6-dicarboxylate, ceric ammonium nitrate (CAN) / acetonitrile; H₂O / a.) 20 min, 0 deg C b.) 10 min, RT

Reference： [1]Keinan, Ehud; Eren, Doron [Journal of Organic Chemistry, 1987, vol. 52, # 17, p. 3872 - 3875]

22
[ 605-94-7 ]
[ 506-13-8 ]
[ 764723-91-3 ]

Yield	Reaction Conditions	Operation in experiment
33%	With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 75℃; for 0.5h;	A solution OF K2S208 (0.450g, 1.66 mmol) in H20 (25 mL) was added dropwise over 2.5 hours to a stirred suspension OF AGN03 (0.262 g, 1.54 mmol), 16-hydroxyhexadecanoic acid (0.408g, 1.50 mmol), and 2,3- DIMETHOXY-5-METHYL-1, 4-benzoquinone (0. 271G, 1.49 mmol) in H2O : CH3CN (1: 1, 36 ML) held at 75C. After stirring for 30 minutes the mixture was cooled and extracted with ether (4 X 30 ML). The combined organic phase was washed with H20 (2 x 100 mL), NaHCO3 (1 M, 2 x 50 ML) and saturated NaCl (2 x 50 mL). The organic phase was dried (NA2S04), filtered and concentrated in vacuo to give a red oil (0.444g). Column chromatography of the crude oil (silica gel, 15g) and elution with mixtures OF CH2C12 AND ether (0 %, 5% 20%) gave 2- (15-HYDROXYPENTADECYL)-5, 6-DIMETHOXY-3-METHYL- [1, 4] benzoquinone (15) (0.192 g, 33 %) as a red OIL. 1H NMR 6 3.99, 3. 98 (6H, s, OMe), 3.64 (2H, t, J= 6. 5HZ,-CH20H), 2.45 (2H, t, J= 7. 5HZ,-CH2-RING), 1.4-1. 2 (26H, m, -(CH2)13-). Anal. Calcd. for C24H4005 : C, 70.6 ; H, 9.9. Found: C, 70.5 ; H, 9.8%.
25%	With ammonium persulfate; silver nitrate; In water; acetonitrile; at 75℃; for 5h;Darkness;	A solution of (NH4)2S2O8 (1.4 g, 6 mmol) in water (30 mL) was added dropwise over 1 h to a stirred suspension of 36 (0.91 g, 5 mmol), AgNO3 (0.85 g, 5 mmol) and 16-hydroxyhexadecanoic acid (1.5 g, 5.5 mmol) in CH3CN (30 mL) and water (30 mL) at 75 C. The reaction mixture was stirred at 75 C for 4 h in the dark and was then cooled to 23 C. The mixture was extracted with diethyl ether, then washed with saturated aqueous NaHCO3 and brine. The ether phase was dried over anhydrous MgSO4 and filtered, and then the solvent was removed in vacuo. The resulting mixture was purified by silica gel column chromatography to give 43 (510 mg, 25%) as a yellow solid. 1H NMR (400 MHz, CDCl3): delta 3.97(s, 6H), 3.62 (t, J 6.8 Hz, 2H), 2.43 (t, J 6.8 Hz, 2H), 1.99 (s, 3H),1.55 (quint, J 6.8 Hz, 2H), 1.33-1.24 (m, 24H) ppm.

Reference： [1]Patent: WO2005/19232,2005,A1 .Location in patent: Page/Page column 60
[2]European Journal of Medicinal Chemistry,2014,vol. 78,p. 248 - 258
[3]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 6429 - 6441

23
[ 50-00-0 ]
[ 605-94-7 ]
[ 30685-16-6 ]
[ 202843-56-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogenchloride; In water; toluene; at 0 - 20℃; for 3 - 10.5h;	Example 1 - Chloromethylation; A reactor with a volume of 6 I equipped with a mechanical stirrer was filled with 2,3- dimethoxy-5-methylbenzoquinone (128 g, 0.70 mol), parafomaldehyde (54.2 g, 2.7 mol (formaldehyde equivalents), and 5 I of toluene. Concentrated hydrochloric acid (422 g, 4.2 mol HCI) was added to the mixture slowly over a period of 30 minutes via a drop- ping funnel at room temperature. After completion of the addition the mixture was al¬ lowed to stir for another 2.5 h at room temperature, upon which time the remaining sol¬ ids in the reaction mixture were filtered over a frit, the water phase separated, the tolu¬ ene phase dried over MgSO4 and evaporated.The crude mixture contained the desired 2,3-dimethoxy-6-methyl-5-chloromethyl- benzoquinone as the main compound (65%), the mayor side product being 25% of the 6-chloro-2,3-dimethoxy-5-methyl-1 ,4-benzoquinone. This crude oil was further purified via column chromatography over silica, using a 3:1 mixture of heptane and ethyl ace¬ tate as an eluent. The isolated yield was 203g (85 wt-%).; Example 2 - Chloromethylation; To a 4 liter glass-reactor, equipped with a mechanical stirrer, was added 2,3- dimethoxy-6-methylbenzoquinone (300 g, 1 ,62 mol), parafomaldehyde (100 g, 3,3 mol (formaldehyde equivalents), and toluene (3 kg), and the mixture cooled to 00C. Con¬ centrated hydrochloric acid (1000 g, 10,26 mol HCI) was dosed to the stirred mixture slowly over a period of 30 minutes via a dropping funnel. After the HCI addition was complete, the mixture was stirred for another 10h at 00C. The solids contained in the mixture were filtered off over a glass frit, the aqueous phase separated, the toluene EPO <DP n="11"/>phase washed twice with water (1 ,5 kg each) and twice with sat. aq. NaHCO3 (0.75 kg each), dried over MgSO4 and evaporated.The resulting crude reaction mixture (348 g) was dissolved in ethyl acetate and filtered over basic alumina (640 g). The filtrate was concentrated and evaporated. The remain- ing red liquid (291 g) contained 72 wt-% of the desired 6-chloromethyl-2,3-dimethoxy-5 methyl-1 ,4-benzoquinone (and 21 % of the 5-chloro-2,3-dimethoxy-6-methyl-1 ,4- benzoquinone as the major side component).

Reference： [1]Patent: WO2006/32425,2006,A2 .Location in patent: Page/Page column 9-10

24
[ 605-94-7 ]
[ 77-78-1 ]
[ 35896-58-3 ]

Yield	Reaction Conditions	Operation in experiment
		Mitoquinone-C3 (6). The synthetic route to Mitoquinone-C3 is shown in Fig 2A. The starting material, 2,3, 4,5-tetramethoxytoluene (1) (Lipshutz, B. H., Kim, S. -k., Mollard, P. and Stevens, K. L. (1998) Tetrahedron 54,1241- 1253) was prepared by reducing 2, 3-dimethoxy-5-metliyl-1, 4-benzoquinone (COQO) to the hydroquinol (Carpino, L. A., TRIOLO, S. A. and Berglund, R. A. (1989) J. Org. Chem. 54,3303-3310) followed by methylation to give 1 (Lipshutz, B. H., Kim, S. -k., Mollard, P. and Stevens, K. L. (1998) Tetrahedron 54, 1241-1253). A solution of 1 (6.35 g, 29.9 mmol) in dry hexane (80 mL) and N, N, N', N'-tetramethylethylenediamine (8.6 mL) was placed with a flame- dried stirrer bar in a flame-dried Schlenk tube under nitrogen. A hexane solution of n-butyl lithium (1.6 M, 26.2 mL) was slowly added at room temperature and the mixture was cooled and stirred at 0C for LHR. After being cooled TO-78C, dry tetrahydrofuran (THF; 250 ML) was added, and a small aliquot of the reaction mixture was removed, quenched with D20 and examined BY 1H NMR to assure complete metallation. The yellow suspension was then transferred to a second flame-dried Schlenk tube containing CUCN (0.54 g, 6.03 mmol) under nitrogen at-78C. The mixture was warmed to 0C for 10 mins, then cooled to-78 C and allyl bromide (3.62 mL) was added and the reaction was stirred overnight (19 hrs) and allowed to warm to room temperature. The reaction was quenched with 10% aqueous NH4CL (75 ML), and extracted with ether (2 x 200 mL). The combined ethereal extracts were washed with H20 (2 x 150 mL), 10% aqueous NH40H (200 mL) and saturated aqueous NaCl (200 mL). The organic solvents were dried over MgS04, filtered and the solvent removed by rotary evaporation in vacuo to give a crude product (7.25g). Column chromatography on silica gel and elution with 20% ether/hexane gave pure 1, 2,3, 4-TETRAMETHOXY-5-METHYL-6- (2-PROPENYL) BENZENE (2) (YOSHIOKA, T., Nishi, T., Kanai, T. , Aizawa, Y. , Wada, K. , Fujita, T. and HORIKOSHI, H. (1993), Eur. Pat. Appl. EP 549366 Al) (6.05 g, 83.5 %). 1H NMR 8 5.84-5. 98 (1H, M,-CH=C), 4. 88-5. 03 (2H, m, =CH2), 3. 78, 3.80, 3. 90, 3.92 (12H, s, OMe), 3.38 (2H, d, J= 7. 0HZ, AR-CH2), 2.14 (3H, s, Ar-Me) ppm.

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 20681 - 20689
[2]Patent: WO2005/19232,2005,A1 .Location in patent: Page/Page column 52-53

25
[ 605-94-7 ]
[ 802294-64-0 ]
[ 91971-27-6 ]

Yield	Reaction Conditions	Operation in experiment
20%	With ammonium peroxydisulfate; silver nitrate; In water; acetonitrile; at 65℃; for 3.5h;	General procedure: To a solution of coenzyme Q0 1 (1.00 g, 5.4 mmol) in degassed CH3CN (120 mL) at 25 C were added AgNO3 (0.25 g, 1.5 mmol) and propanoic acid (0.48 g, 6.5 mmol). After the mixture was heated to 65 C, (NH4)2S2O8 (2.80 g, 12.5 mmol) in 10 mL degassed H2O was added dropwisely over 30 min17 (see Scheme 3). After 3 h, the reaction mixture was cooled to 25 C and was extracted with EtOAc (3×150 mL), and the organic layers were washed with brine (150 mL), dried (MgSO4), and concentrated. The crude product was purified by silica chromatography to give 4 (20%). 1H NMR (500.0 MHz, CDCl3, 298 K): 3.99 (s, 3H, -OCH3), 4.00 (s, 3H, -OCH3), 2.02 (s, 3H, -CH3), 1.05 (t, 3H, -CH2CH3), 2.45 (q, 2H, -CH2CH3) ppm.

Reference： [1]Tetrahedron,2011,vol. 67,p. 5990 - 6000

26
[ 605-94-7 ]
[ 1431987-73-3 ]
[ 1431987-20-0 ]

Yield	Reaction Conditions	Operation in experiment
6%	With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 75℃; for 3h;	To a solution of 2,3-dimethoxy-5-methyl-p-benzoquinone (0.774 g, 4.01 mmol), 9-(nitrooxy)nonanoic acid (0.90 g, 4.01 mmol)(synthesized as in Example 28, steps 2 and 3) and AgNO3 (0.68 g, 4.01 mmol)in CH3CN (25 ml) heated at 75C, a solution of K2S2O8 (1.30 g, 4.81 mmol) in H2O (25 ml) was added dropwise. The reaction mixture was stirred at 75C for 3 hours, then it was allowed to cool to room temperature, and was poured in H2O (50 ml). The product was extracted with EtOAc (2 X 30 ml). The combined organic layers were washed with NaHCO3 sat. solution and brine, dried on Na2SO4 and concentrated. The residue was purified by flash chromatography (Biotage SP1 instrument, SNAP 50 g column, Hex/EtOAc 9: 1 in 15 CV) affording 80 mg (Yield: 6%)of the title compound ad a red oil. 1H NMR (300 MHz, CDC13) delta 4.50-4.36 (m, 2H), 3.99 (s, 6H), 2.53- 2.36 (m, 2H), 2.01 (s, 3H), 1.81 - 1.62 (m, 2H), 1.45 - 1.26 (m, 10H).
6%	With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 75℃; for 3h;	Example 36 Synthesis of 8-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-l,4- dienyl)octyl nitrate (compound (33)) To a solution of 2,3-dimethoxy-5-methyl-p-benzoquinone (0.774 g, 4.01 mmol), 9-(nitrooxy)nonanoic acid (0.90 g, 4.01 mmol)(synthesized as in Example 28, steps 2 and 3) and AgNO3 (0.68 g, 4.01 mmol)in CH3CN (25 ml) heated at 75C, a solution of K2S2O8 (1.30 g, 4.81 mmol) in H2O (25 ml) was added dropwise. The reaction mixture was stirred at 75C for 3 hours, then it was allowed to cool to room temperature, and was poured in H2O (50 ml). The product was extracted with EtOAc (2 X 30 ml). The combined organic layers were washed with NaHCO3 sat. solution and brine, dried on Na2SO4 and concentrated. The residue was purified by flash chromatography (Biotage SP1 instrument, SNAP 50 g column, Hex/EtOAc 9: 1 in 15 CV) affording 80 mg (Yield: 6%)of the title compound ad a red oil. 1H NM (300 MHz, CDC13) delta 4.50-4.36 (m, 2H), 3.99 (s, 6H), 2.53-2.36 (m, 2H), 2.01 (s, 3H), 1.81 - 1.62 (m, 2H), 1.45 - 1.26 (m, 10H).

Reference： [1]Patent: WO2013/60673,2013,A1 .Location in patent: Page/Page column 89-90
[2]Patent: WO2014/63923,2014,A1 .Location in patent: Page/Page column 84

27
[ 605-94-7 ]
[ 74754-55-5 ]
[ 1431986-93-4 ]

Yield	Reaction Conditions	Operation in experiment
8%	With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 75℃; for 5h;	To a solution of 2,3-dimethoxy-5-methyl-p-benzoquinone (0.93 g, 5.12 mmol), 6-(nitrooxy)hexanoic acid (0.93 g, 5.12 mmol) (prepared as described in Example 2, Step 2) and AgNO3 (1.04 g, 6.14 mmol)in CH3CN (50 ml) heated at 75C, a solution of K2S2O8 (1.66 g, 6.14 mmol) in H2O (50 ml) was added dropwise. The reaction mixture was stirred at 75C for 5 hours, then it was allowed to cool to room temperature, and was poured in H2O (50 ml). The product was extracted with EtOAc (2 X 30 ml). The combined organic layers were washed with NaHCO3 sat. solution and brine, dried on Na2SO4 and concentrated. The residue was purified by flash chromatography (Biotage SPl instrument, SNAP 100 g column, EtOAc in Hex from 5% to 40% in 10 CV) affording 130 mg (yield: 8%) of the title compound as an orange oil. 1H NMR (300 MHz, CDC13) delta 4.53-4.59 (m, 2H), 3.98 (s, 6H), 2.55- 2.38 (m, 2H), 2.02 (s, 3H), 1.87-1.64 (m, 2H), 1.52 - 1.37 (m, 4H).
8%	With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 75℃; for 5h;	Example 3 Synthesis of 5-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-l,4- dienyl)pentyl nitrate (compound (2)) (2) To a solution of 2,3-dimethoxy-5-methyl-p-benzoquinone (0.93 g, 5.12 mmol), 6-(nitrooxy)hexanoic acid (0.93 g, 5.12 mmol) (prepared as described in Example 2, Step 2) and AgNO3 (1.04 g, 6.14 mmol)in CH3CN (50 ml) heated at 75C, a solution of K2S2O8 (1.66 g, 6.14 mmol) in H2O (50 ml) was added dropwise. The reaction mixture was stirred at 75C for 5 hours, then it was allowed to cool to room temperature, and was poured in H2O (50 ml). The product was extracted with EtOAc (2 X 30 ml). The combined organic layers were washed with NaHCO3 sat. solution and brine, dried on Na2SO4 and concentrated. The residue was purified by flash chromatography (Biotage SP1 instrument, SNAP 100 g column, EtOAc in Hex from 5% to 40% in 10 CV) affording 130 mg (yield: 8%) of the title compound as an orange oil. 1H NMR (300 MHz, CDC13) delta 4.53-4.59 (m, 2H), 3.98 (s, 6H), 2.55-2.38 (m, 2H), 2.02 (s, 3H), 1.87-1.64 (m, 2H), 1.52 - 1.37 (m, 4H).

Reference： [1]Patent: WO2013/60673,2013,A1 .Location in patent: Page/Page column 30-31
[2]Patent: WO2014/63923,2014,A1 .Location in patent: Page/Page column 32-33

28
[ 605-94-7 ]
[ 944916-36-3 ]
[ 1431986-99-0 ]

Yield	Reaction Conditions	Operation in experiment
7%	With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 75℃; for 3h;	To a solution of 2,3-dimethoxy-5-methyl-p-benzoquinone (1.04 g, 5.72 mmol), 7-(nitrooxy)heptanoic acid (1.10 g, 5.72 mmol) and AgNO3 (0.97 g, 5.72 mmol)in CH3CN (50 ml) heated at 75C, a solution of K2S2O8 (1.55 g, 5.72 mmol) in H2O (50 ml) was added dropwise. The reaction mixture was stirred at 75C for 3 hours, then it was allowed to cool to room temperature, and was poured in H2O (50 ml). The product was extracted with EtOAc (2 X 30 ml). The combined organic layers were washed with NaHCO3 sat. solution and brine, dried on Na2SO4 and concentrated. The residue was purified by flash chromatography (Biotage SPl instrument, SNAP 50 g column, EtOAc in Hex from 5% to 50% in 10 CV) affording 125 mg (Yield: 7%)of the title compound ad a red oil. 1H NMR (300 MHz, CDC13) delta 4.50-4.38 (m, 2H), 3.96 (s, 6H), 2.54- 2.36 (m, 2H), 2.01 (s, 3H), 1.83 - 1.64 (m, 2H), 1.52 - 1.31 (m, 6H).
7%	With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 75℃; for 3h;	Example 15 Synthesis of 6-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-l,4- dienyl)hexyl nitrate (compound (16)) (16) To a solution of 2,3-dimethoxy-5-methyl-p-benzoquinone (1.04 g, 5.72 mmol), 7-(nitrooxy)heptanoic acid (1.10 g, 5.72 mmol) and AgNO3 (0.97 g, 5.72 mmol)in CH3CN (50 ml) heated at 75C, a solution of K2S2O8 (1.55 g, 5.72 mmol) in H2O (50 ml) was added dropwise. The reaction mixture was stirred at 75C for 3 hours, then it was allowed to cool to room temperature, and was poured in H2O (50 ml). The product was extracted with EtOAc (2 X 30 ml). The combined organic layers were washed with NaHCO3 sat. solution and brine, dried on Na2SO4 and concentrated. The residue was purified by flash chromatography (Biotage SP1 instrument, SNAP 50 g column, EtOAc in Hex from 5% to 50% in 10 CV) affording 125 mg (Yield: 7%)of the title compound ad a red oil. 1H NMR (300 MHz, CDC13) delta 4.50-4.38 (m, 2H), 3.96 (s, 6H), 2.54-2.36 (m, 2H), 2.01 (s, 3H), 1.83 - 1.64 (m, 2H), 1.52 - 1.31 (m, 6H).

Reference： [1]Patent: WO2013/60673,2013,A1 .Location in patent: Page/Page column 53-54
[2]Patent: WO2014/63923,2014,A1 .Location in patent: Page/Page column 49-50

29
[ 605-94-7 ]
[ 74754-56-6 ]
[ 1431987-00-6 ]

Yield	Reaction Conditions	Operation in experiment
10%	With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 75℃; for 3h;	To a solution of 2,3-dimethoxy-5-methyl-p-benzoquinone (0.54 g, 2.95 mmol), 5-(nitrooxy)pentanoic acid (0.48 g, 2.95 mmol) and AgNO3 (0.50 g, 2.95 mmol)in CH3CN (15 ml) heated at 75C, a solution of K2S2O8 (0.96 g, 3.54 mmol) in H2O (15 ml) was added dropwise. The reaction mixture was stirred at 75C for 3 hours, then it was allowed to cool to room temperature, and was poured in H2O (10 ml). The product was extracted with EtOAc (2 X 10 ml). The combined organic layers were washed with NaHCO3 sat. solution and brine, dried on Na2SO4 and concentrated. The residue was purified by flash chromatography (Biotage SPl instrument, SNAP 50 g column, EtOAc in Hex from 5% to 40% in 15 CV) affording 90 mg of a red oil (Yield: 10%). 1H NMR (300 MHz, CDC13) delta 4.47 (t, 2H), 3.99 (s, 6H), 2.61 - 2.42 (m, 2H), 2.03 (s, 3H), 1.86 - 1.69 (m, 2H), 1.60 - 1.41 (m, 2H).
10%	With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 75℃; for 3h;	Example 16 Synthesis of 4-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-l,4- dienyl)butyl nitrate (compound (4)) (4) To a solution of 2,3-dimethoxy-5-methyl-p-benzoquinone (0.54 g, 2.95 mmol), 5-(nitrooxy)pentanoic acid (0.48 g, 2.95 mmol) and AgNO3 (0.50 g, 2.95 mmol)in CH3CN (15 ml) heated at 75C, a solution of K2S2O8 (0.96 g, 3.54 mmol) in H2O (15 ml) was added dropwise. The reaction mixture was stirred at 75C for 3 hours, then it was allowed to cool to room temperature, and was poured in H2O (10 ml). The product was extracted with EtOAc (2 X 10 ml). The combined organic layers were washed with NaHCO3 sat. solution and brine, dried on Na2SO4 and concentrated. The residue was purified by flash chromatography (Biotage SP1 instrument, SNAP 50 g column, EtOAc in Hex from 5% to 40% in 15 CV) affording 90 mg of a red oil (Yield: 10%). 1H NMR (300 MHz, CDC13) delta 4.47 (t, 2H), 3.99 (s, 6H), 2.61 - 2.42 (m, 2H), 2.03 (s, 3H), 1.86 - 1.69 (m, 2H), 1.60 - 1.41 (m, 2H).

Reference： [1]Patent: WO2013/60673,2013,A1 .Location in patent: Page/Page column 54
[2]Patent: WO2014/63923,2014,A1 .Location in patent: Page/Page column 50

30
[ 605-94-7 ]
[ 2834-05-1 ]
[ 81575-48-6 ]

Yield	Reaction Conditions	Operation in experiment
20%		General procedure: A solution of (NH4)2S2O8(1.4 g, 6 mmol) in water (30mL) was added dropwise over 1 h to a stirred suspension of 19 (0.75 g,5 mmol), AgNO3 (0.85 g, 5 mmol) and 11-Bromoundecanoic acid (1.5 g, 5.5mmol) in CH3CN (30 mL)and water (30 mL) at 75 . The reaction mixture was stirredat 75 for 4 hours in the dark and then cooled to 23 .Subsequently, CH3CN was removed. The mixture was extracted withdiethyl ether (3x30 mL). The ether phase was washed with saturated aqueousNaHCO3 solution and brine. The ether phase was dried over anhydrousMgSO4 and filtered, and then the solvent was removed in vacuo. Theresulting mixture was purified by silica gel column chromatography to give 29(0.4 g, 22%) as a yellow solid.1H NMR (400 MHz, CDCl3): delta 3.40 (t, J = 6.8 Hz,2H), 2.45 (t, J = 6.8 Hz, 2H), 2.00(s, 9H), 1.84 (q, J = 6.8 Hz, 2H),1.43-1.25 (m, 14H) ppm. 13CNMR (125 MHz, CDCl3): delta 187.8,187.2, 144.5, 140.4, 140.3, 140.0, 34.0, 32.8, 29.9, 29.4, 29.3, 28.8, 28.7,28.1, 26.6, 12.32, 12.30, 12.1 ppm. MS (ESI, m/z): 369 (M++1).
20%	With ammonium persulfate; silver nitrate; In water; acetonitrile; at 75℃; for 4h;Darkness;	A solution of (NH4)2S2O8 (1.4 g, 6 mmol) in water (30 mL) was added dropwise over 1 h to a stirred suspension of 36 (0.91 g, 5 mmol), AgNO3 (0.85 g, 5 mmol) and 11-Bromoundecanoic acid (1.5 g, 5.5 mmol) in CH3CN (30 mL) and water (30 mL) at 75 C. The reaction mixture was stirred at 75 C for 4 h in the dark and was then cooled to 23 C, the mixture was extracted with diethyl ether, then washed with saturated aqueous NaHCO3 and brine. The ether phase was dried over anhydrous MgSO4 and filtered, and then the solvent was removed in vacuo at room temperature. The resulting mixture was purified by silica gel column chromatography to give 38 (0.4 g, 20%) as a yellow solid. 1H NMR (400 MHz, CDCl3): delta 3.98 (s,6H), 3.38 (t, J 6.8 Hz, 2H), 2.43 (t, J 6.8 Hz, 2H), 1.99 (s, 3H), 1.85-1.81 (m, 2H), 1.42-1.18 (m, 14H) ppm. 13C NMR (125 MHz, CDCl3): delta 188.1, 184.0, 155.5, 144.7, 138.5, 128.6, 60.8, 34.0, 32.8, 29.9, 29.4,29.3, 28.8, 28.7, 28.1, 26.7, 11.7 ppm. MS (ESI, m/z): 401 (M+ + 1).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1650 - 1653
[2]European Journal of Medicinal Chemistry,2014,vol. 78,p. 248 - 258

31
[ 605-94-7 ]
[ 30515-28-7 ]
[ 1608463-91-7 ]

Yield	Reaction Conditions	Operation in experiment
20%	With ammonium persulfate; silver nitrate; In water; at 75℃; for 5h;Darkness;	A solution of (NH4)2S2O8 (1.4 g, 6 mmol) in water (30 mL) was added dropwise over 1 h to a stirred suspension of 36 (0.91 g,5 mmol), AgNO3 (0.85 g, 5 mmol) and 7-Bromoheptanoic acid (1.1 g,5.5 mmol) in CH3CN (30 mL) and water (30 mL) at 75 C. The reaction mixture was stirred at 75 C for 4 h in the dark and was then cooled to 23 C, the mixture was extracted with diethyl ether, then washed with saturated aqueous NaHCO3 and brine. The ether phase was dried over anhydrous MgSO4 and filtered, and then the solvent was removed in vacuo at room temperature. The resulting mixture was purified by silica gel column chromatography to give 42 (0.35 g,20%) as a yellow solid. 1H NMR (400 MHz, CDCl3): delta 3.98 (s, 6H), 3.40(t, J 6.8 Hz, 2H), 2.45 (t, J 6.8 Hz, 2H), 2.00 (s, 3H), 1.88 (quint,J 6.8 Hz, 2H), 1.47e1.36 (m, 6H) ppm. 13C NMR (125 MHz, CDCl3): delta 184.6, 184.1, 144.3, 142.7, 138.8, 61.1, 33.8, 32.6, 28.9, 28.4, 27.8,26.2, 11.9 ppm. MS (ESI, m/z): 345 (M+ + 1).

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 248 - 258

32
[ 605-94-7 ]
[ 1679-53-4 ]
[ 77712-32-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 75℃; for 4h;	To a solution of coenzyme Q0 (1.20 g, 6.59 mmol) and <strong>[1679-53-4]10-hydroxydecanoic acid</strong> (2, 1.50 g, 7.91 mmol) in MeCN (20 mL) and distilled H2O (20 mL) was added AgNO3 (0.67 g, 3.95 mmol). The mixture was heated to 75 C and a solution of K2S2O8 (2.50 g, 9.22mmol) in distilled H2O (30 mL) was added dropwise over 2 h; then the reaction mixture was stirred for another 2 h, with TLC monitoring until the starting material was consumed. The resulting mixture was cooled and extracted with CH2Cl2; the organic layer was washed with H2O, then dried (anhyd Na2SO4), and evaporated under reduced pressure. The residue was purified by column chromatograph(silica gel, petroleum ether-EtOAc, 4:1) to give product 3 (1.34 g, 60% isolated yield) as yellow needles; mp 42-44 C(Lit.6a 45 C).1H NMR (400 MHz, CDCl3): delta = 3.91 (s, 6 H), 3.57-3.53 (t, J = 6.3Hz, 2 H), 2.52 (br s, 1 H), 2.37-3.35 (m, 2 H), 2.00 (s, 3 H), 1.48-1.47 (m, 2 H), 1.22 (br s, 12 H).13C NMR (100 MHz, acetone-d6): delta = 184.5, 183.9, 144.0, 142.8 (2C), 138.5, 62.6, 60.9, 32.5, 29.6, 29.2, 29.1, 29.0, 28.5, 26.2, 25.5,11.7.MS (ESI): m/z = 325 (M+ + H).
60%	With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 75℃; for 2h;	To a solution of Coenzyme Q0 2 (0.55 g, 3 mmol) and 10-hydroxycapricacid (0.70 g, 3.6 mmol) in acetonitrile 10 mL and distilled water 10 mL was added AgNO3 (0.50 g, 3 mmol). The mixture was heated to 75 C, a solution of K2S2O8 (1.62 g, 6 mmol) in distilled water 20 mL was added dropwise over 2 h. The reaction was monitored by TLC until the starting material was consumed.The resulting mixture was cooled and extracted with CH2Cl2 andwashed with water, then dried over anhydrous Na2SO4 and evaporated under reduced pressure, and the residue was purified by column chromatograph on silica gel (PE/EtoAc 4:1) to give an orange oil 3 (0.97 g) in 60% yield.1H NMR (400 MHz, CDCl3): 3.91 (s, 6H, OCH3), 3.55 (t, J 6.3 Hz,2H, CH2OH), 2.52 (brs, 1H, OH), 2.37e3.35 (m, 2H), 2.00 (s, 3H, CH3),1.48-1.47 (m, 2H), 1.22 (brs, 12H). 13C MR (100 MHz, (CD3)2CO):184.5, 183.9, 144.0,142.8 (2C),138.5, 62.6, 60.9, 32.5, 29.6, 29.2, 29.1,29.0, 28.5, 26.2, 25.5, 11.7. MS (ESI): m/z 325 (MH).

Reference： [1]Synthesis,2014,vol. 46,p. 2371 - 2375
[2]European Journal of Medicinal Chemistry,2014,vol. 86,p. 710 - 713

33
[ 79-14-1 ]
[ 605-94-7 ]
[ 84055-96-9 ]

Yield	Reaction Conditions	Operation in experiment
20%		General procedure: To a solution of Coenzyme Q0 1 (1.09 g, 6 mmol) and 11-mono-carboxylic acids 2 or 4 (7.8 mmol) in acetonitrile 40 mL and distilled water 10 mL was added AgNO3 (0.31 g, 1.8 mmol). The mixture was heated to 75 C and a solution of K2S2O8 (3.24 g, 12 mmol) in distilled water 30 mL was added dropwise over 2 h, then the reaction mixture was stirred for another 1 h. The resulting mixture was cooled and extracted with CH2Cl2 and the organic layer was washed with water, then dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by short column chromatograph on silica gel (eluent: PE/EtOAc=3:1 or 5:1) to give idebenone 3 or Coenzyme Q analogues 5.

Reference： [1]Tetrahedron,2014,vol. 70,p. 9029 - 9032

34
[ 605-94-7 ]
[ 79-11-8 ]
[ 202843-56-9 ]

Yield	Reaction Conditions	Operation in experiment
18%		General procedure: To a solution of Coenzyme Q0 1 (1.09 g, 6 mmol) and 11-mono-carboxylic acids 2 or 4 (7.8 mmol) in acetonitrile 40 mL and distilled water 10 mL was added AgNO3 (0.31 g, 1.8 mmol). The mixture was heated to 75 C and a solution of K2S2O8 (3.24 g, 12 mmol) in distilled water 30 mL was added dropwise over 2 h, then the reaction mixture was stirred for another 1 h. The resulting mixture was cooled and extracted with CH2Cl2 and the organic layer was washed with water, then dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by short column chromatograph on silica gel (eluent: PE/EtOAc=3:1 or 5:1) to give idebenone 3 or Coenzyme Q analogues 5.

Reference： [1]Tetrahedron,2014,vol. 70,p. 9029 - 9032

35
[ 605-94-7 ]
[ 625-45-6 ]
[ 84056-01-9 ]

Yield	Reaction Conditions	Operation in experiment
32%		General procedure: To a solution of Coenzyme Q0 1 (1.09 g, 6 mmol) and 11-mono-carboxylic acids 2 or 4 (7.8 mmol) in acetonitrile 40 mL and distilled water 10 mL was added AgNO3 (0.31 g, 1.8 mmol). The mixture was heated to 75 C and a solution of K2S2O8 (3.24 g, 12 mmol) in distilled water 30 mL was added dropwise over 2 h, then the reaction mixture was stirred for another 1 h. The resulting mixture was cooled and extracted with CH2Cl2 and the organic layer was washed with water, then dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by short column chromatograph on silica gel (eluent: PE/EtOAc=3:1 or 5:1) to give idebenone 3 or Coenzyme Q analogues 5.

Reference： [1]Tetrahedron,2014,vol. 70,p. 9029 - 9032

36
[ 605-94-7 ]
[ 627-03-2 ]
[ 1340548-39-1 ]

Yield	Reaction Conditions	Operation in experiment
35%		General procedure: To a solution of Coenzyme Q0 1 (1.09 g, 6 mmol) and 11-mono-carboxylic acids 2 or 4 (7.8 mmol) in acetonitrile 40 mL and distilled water 10 mL was added AgNO3 (0.31 g, 1.8 mmol). The mixture was heated to 75 C and a solution of K2S2O8 (3.24 g, 12 mmol) in distilled water 30 mL was added dropwise over 2 h, then the reaction mixture was stirred for another 1 h. The resulting mixture was cooled and extracted with CH2Cl2 and the organic layer was washed with water, then dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by short column chromatograph on silica gel (eluent: PE/EtOAc=3:1 or 5:1) to give idebenone 3 or Coenzyme Q analogues 5.

Reference： [1]Tetrahedron,2014,vol. 70,p. 9029 - 9032

37
[ 3669-80-5 ]
[ 605-94-7 ]
[ 58186-27-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dihydrogen peroxide; oxygen; In water; acetone; at 75℃;Catalytic behavior;	Weigh coenzyme Q0 1.2g, 11-hydroxyundecanoic acid 1.50g, copper chloride catalyst 0.2g, placed in a thermometer inserted 250ml round bottom flask was added 30 ml of acetone and 30 ml of water sonicate to dissolve, warmed to 75 C,under an oxygen protected. It was slowly added dropwise 30% hydrogen peroxide oxidizer 20mL, dropwise over 2 hours, incubation was continued for 2 h. TLCmonitoring gusset starting material transShould be complete, the reaction was stopped, 50mLwater was added immediatelyquenched reaction was extracted three times with dichloromethane 40mL,organic layers were combined, washed with saturatedAnd washed with salt to neutral, dried over anhydrous sodium sulfate and evaporated under reduced pressure to give a red liquid. Column chromatography (petroleum ether: ethyl acetate4: 1) to give yellow needles, 80% yield.
65%		General procedure: To a solution of Coenzyme Q0 1 (1.09 g, 6 mmol) and 11-mono-carboxylic acids 2 or 4 (7.8 mmol) in acetonitrile 40 mL and distilled water 10 mL was added AgNO3 (0.31 g, 1.8 mmol). The mixture was heated to 75 C and a solution of K2S2O8 (3.24 g, 12 mmol) in distilled water 30 mL was added dropwise over 2 h, then the reaction mixture was stirred for another 1 h. The resulting mixture was cooled and extracted with CH2Cl2 and the organic layer was washed with water, then dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by short column chromatograph on silica gel (eluent: PE/EtOAc=3:1 or 5:1) to give idebenone 3 or Coenzyme Q analogues 5.

Reference： [1]Patent: CN107011146,2017,A .Location in patent: Paragraph 0021; 0024; 0026; 0028; 0030; 0032; 0034
[2]New Journal of Chemistry,2020,vol. 44,p. 8702 - 8704
[3]Tetrahedron,2014,vol. 70,p. 9029 - 9032

38
[ 605-94-7 ]
[ 62-53-3 ]
2,3-dimethoxy-5-methyl-6-(phenylamino)cyclohexa-2,5-diene-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	In ethanol; at 20℃; for 2h;	General procedure: To a solution of 2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (0.18 g, 1 mmol) in alcohol 10 mL was added aniline (0.1g, 1.1 mmol), the mixture was stirred at rt for 2 h. The reaction mixture was concentrated in vacuo, and the crude residue was purified by column chromatography on silica gel (EtOAc / petroleum ether = 1 / 20) to yield the title compound (0.18 g, 66 %) as A dark purple solid solid. 1H NMR (400 MHz, CDCl3) delta 7.30 (t, J = 7.9 Hz, 2H), 7.16 (s, 1H), 7.08 (d, J = 7.4 Hz, 1H), 6.92 (d, J = 8.0 Hz, 2H), 4.12 (s, 3H), 3.92 (s, 3H), 1.55 (s, 3H). 13C NMR (126 MHz, CDCl3) delta 183.5, 182.0, 147.2, 140.8, 139.7, 139.3, 129.0, 124.3, 122.4, 112.7, 61.5, 61.3, 13.0. MS (ESI): m/z 296.5 [M+Na]+
57%	In ethanol; at 20℃; for 2h;	<strong>[605-94-7]2,3-dimethoxy-5-methyl-1,4-benzoquinone</strong> (1.00 mmol)Dissolve with aniline (1.00mmol) in ethanol and react at room temperature for 2 hours,Evaporate the solvent, column chromatography to obtain bluePurple solid target compound,The yield was 57%.

Reference： [1]Bioorganic Chemistry,2019,vol. 89
[2]Patent: CN110950749,2020,A .Location in patent: Paragraph 0155-0158

39
[ 614-45-9 ]
[ 605-94-7 ]
[ 483-54-5 ]

Yield	Reaction Conditions	Operation in experiment
53%	With bismuth(lll) trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 100℃; for 2h;Sealed tube; Green chemistry;	General procedure: To a sealed tube were added quinones 1 (0.4 mmol), Bi(OTf)3 (5 mol%), TBPB (1.2 mmol) and DCE (2 ml). Then, reaction mixture was stirred at 100C for 4h or for the time indicated in Table 2. After the completion of the reaction, the reaction was quenched with saturated Na2SO3 (2 ml) and saturated brine (2 ml). The mixture was extracted with EA (3×5 mL). The combined organic layer was dried over anhydrous Mg2SO4 and concentrated under reduced pressure. The crude products were purified on a silica gel column using PE/EA to give 2a-r.

Reference： [1]Tetrahedron,2019,vol. 75

40
[ 605-94-7 ]
[ 870-63-3 ]
[ 727-81-1 ]

Yield	Reaction Conditions	Operation in experiment
70%		1-Bromo-3-methyl-2-butene (1; 1.49 g, 0.01 mol), Hantzsch ester (0.25 g, 1 mmol), and CoQ0 (1.82 g,0.01 mol) were dissolved in dichloromethane (10 mL) under a nitrogen atmosphere. After stirring for 30 min, a solution of BF3·Et2O (1.2 mL, 0.01 mol) in dichloromethane (1 mL) was added, and the solution was stirred at r.t. for 2 h. The mixture was extracted with CH2Cl2 (3 × 10 mL). The combined organic phases were washed with H2O and brine, then dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (PE/EtOAc, 8:1) to give CoQ1.1H NMR (400 MHz, CDCl3): delta = 4.32 (t, 1H, J = 7.0 Hz,C=CH), 3.96 (s, 3H, CH3O), 3.94 (s, 3H, CH3O), 3.12 (d,2H, J = 7.0 Hz, CH2), 2.14 (s, 3H, CH3), 1.75 (s, 3H, CH3),1.65 (s, 3H, CH3).13C NMR (101 MHz, CDCl3): delta = 180.0 (C=O),175.6(C=O), 144.1, 143.0, 142.7, 132.6, 126.5, 123.4, 60.5(OCH3), 60.3 (OCH3), 30.4, 29.1, 25.4, 15.7(CH3).MS (ESI): m/z = 251 [M + H]+.The spectroscopic data are in accord with the literature.

Reference： [1]Journal of Chemical Research,2019,vol. 43,p. 553 - 556

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CAS No. :	605-94-7	MDL No. :	MFCD00001595
Formula :	C₉H₁₀O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UIXPTCZPFCVOQF-UHFFFAOYSA-N
M.W :	182.17	Pubchem ID :	69068
Synonyms :	Coenzyme Q0;CoQ0;2,3-Dimethoxy-5-methyl-p-benzoquinone

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.88
TPSA :	52.6 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.84 cm/s

Log Po/w (iLOGP) :	1.84
Log Po/w (XLOGP3) :	0.8
Log Po/w (WLOGP) :	0.59
Log Po/w (MLOGP) :	-0.95
Log Po/w (SILICOS-IT) :	1.32
Consensus Log Po/w :	0.72

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Log S (ESOL) :	-1.34
Solubility :	8.3 mg/ml ; 0.0456 mol/l
Class :	Very soluble
Log S (Ali) :	-1.49
Solubility :	5.95 mg/ml ; 0.0327 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.69
Solubility :	3.73 mg/ml ; 0.0205 mol/l
Class :	Soluble

PAINS :	1.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.89

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

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P378
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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.
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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
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P401
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P411 + P235	Keep cool.
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P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 605-94-7 ] {[proInfo.proName]}

Quality Control of [ 605-94-7 ]

Related Doc. of [ 605-94-7 ]

Product Details of [ 605-94-7 ]

Calculated chemistry of [ 605-94-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 605-94-7 ]

Application In Synthesis of [ 605-94-7 ]

[ 605-94-7 ] Synthesis Path-Downstream 1~40

Related Functional Groups of [ 605-94-7 ]

Ethers

Ketones

Precautionary Statements-General

Prevention

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Inquiry

Related Functional Groups of
[ 605-94-7 ]