527-61-7

Basic information

• Product Name: 2,6-DIMETHYLBENZOQUINONE
• Synonyms: 2,5-Cyclohexadiene-1,4-dione,2,6-dimethyl-;2,6-Dimethyl-1,4-quinone;2,6-Dimethylbenzo-1,4-quinone;2,6-dimethyl-p-benzoquinon;2,6-Dimethylquinone;3,5-dimethylbenzoquinone;4-dione,2,6-dimethyl-5-cyclohexadiene-1;p-Benzoquinone, 2,6-dimethyl-
• CAS NO: 527-61-7
• Molecular Formula: C8H8O2
• Molecular Weight: 136.15
• EINECS: 208-420-8
• Product Categories: Anthraquinones, Hydroquinones and Quinones;Benzoquinones;Benzoquinones, etc. (Charge Transfer Complexes);Charge Transfer Complexes for Organic Metals;Functional Materials;C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 527-61-7.mol
• Article Data: 143

Chemical Properties

• Melting Point: 71-73 °C(lit.)
• Boiling Point: 201℃
• Flash Point: 71℃
• Appearance: Yellow to brown/Needle-Like Crystalline Solid
• Density: 1.115
• Refractive Index: 1.
• Water Solubility: Soluble in chloroform. Insoluble in water.
• Stability: Stable. Combustible. Incompatible with oxidizing agents.
• BRN: 2041345
• CAS DataBase Reference: 2,6-DIMETHYLBENZOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIMETHYLBENZOQUINONE(527-61-7)
• EPA Substance Registry System: 2,6-DIMETHYLBENZOQUINONE(527-61-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• RTECS: DK4825000
• Hazardous Substances Data: 527-61-7(Hazardous Substances Data)

Usage

Chemical Properties

yellow solid

Uses

2,6-Dimethyl-p-benzoquinone is used as organic intermediates.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 728, 1989 DOI: 10.1021/jo00264a047

InChI:InChI=1/C8H8O2/c1-5-3-7(9)4-6(2)8(5)10/h3-4H,1-2H3

Synthetic route

1,4-dihydroxy-2,6-dimethylbenzene (654-42-2) → 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With nitric acid; sodium nitrite In methanol at -10℃;	100%
With dihydrogen peroxide; bis-(tributyltin oxide) dioxochromium(VI) In benzene at 50℃; for 2h;	91%
With air; cobalt(II) phthalocyanine; Montmorillonite K10 In 1,4-dioxane; water at 20℃; for 6h;	90%

2.6-dimethylphenol (576-26-1) → 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With titanium superoxide; dihydrogen peroxide; acetic acid In water at 50℃; for 2h;	97%
With Oxone; sodium iodide; benzene In water; acetonitrile at 40℃; Reagent/catalyst; Temperature;	96%
With [N,N'-bis(salicylidene)ethane-1,2-diaminato]cobalt(II); oxygen In N,N-dimethyl-formamide	95%

2.6-dimethylphenol (576-26-1) → 1,4-dihydroxy-2,6-dimethylbenzene (654-42-2) + 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With dihydrogen peroxide; Ti-superoxide In water; acetic acid at 50 - 60℃; for 1.25h; Product distribution / selectivity;	A 2% B 97%

3,5-Dimethylphenol (108-68-9) → 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With oxygen In water; acetonitrile at 40℃; under 15001.5 Torr; for 1h; Green chemistry;	90%
With tert.-butylhydroperoxide In decane; acetonitrile at 70℃; for 3h; Catalytic behavior; regioselective reaction;	88%
With 2,6-dicarboxypyridinium fluorochromate at 20℃; for 0.166667h;	86%

4,4-dimethoxy-3,5-dimethylcyclohexa-2,5-dien-1-one (116760-59-9) → 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With sulfuric acid In 1,2-dimethoxyethane for 1h; Hydrolysis; Heating;	90%

2,6-dimethylaniline (87-62-7) → 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With cerium(IV) chlorate; 4-amino-phenol In perchloric acid for 2h;	88%
Oxydation;
With potassium nitrososulfonate

4-bromo-2,6-dimethyl-phenol (2374-05-2) → 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With oxygen; copper dichloride In water; N,N-dimethyl-formamide at 60℃; for 16h;	88%

Mesitol (527-60-6) → 4-hydroxy-3,5-dimethylbenzaldehyde (2233-18-3) + 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With oxygen; acetone oxime In various solvent(s) at 40℃; under 860.3 Torr; for 6h;	A 87% B 4%
With oxygen In various solvent(s) at 60℃; under 860.3 Torr; for 5h; Product distribution; Mechanism; Rate constant; var. aditives, times, solvents;	A 77.7% B 3.7%
With oxygen; diethylamine In various solvent(s) at 60℃; under 860.3 Torr; for 4h; Product distribution; other amines; variation of condition;
With oxygen; diethylamine In various solvent(s) at 60℃; under 860.3 Torr; for 4h; Yield given. Yields of byproduct given;

2,6-dimethyl-4-chlorophenol (1123-63-3) → 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With oxygen In methanol at 21.85℃; Irradiation;	86%

2,5-dimethylbenzamide (55321-98-7) → 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With sodium hydrogen sulfate; [bis(acetoxy)iodo]benzene In water; acetonitrile at 20℃; for 0.666667h;	85%

2.6-dimethylphenol (576-26-1) → 3,3',5,5'-tetramethyldiphenoquinone (4906-22-3) + 4-hydroxy-3,5-dimethylphenyl acetate (880-06-8) + 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With manganese triacetate; ammonium chloride In acetic acid at 100℃; for 0.333333h;	A 84% B 6% C 2%

Mesitol (527-60-6) → 2,6-dimethyl-1,4-benzoquinone (527-61-7) + 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl (2417-04-1) + 3,3',5,5'-tetramethyl-4,4'-diphenoquinone

Conditions	Yield
With C34H24Cl4Cu2FeN10O4(1-)*C8H20N(1+); oxygen; sodium hydroxide In methanol at 25℃; for 6h;	A 80% B 4% C 6%

2.6-dimethylphenol (576-26-1) → 2,6-dimethyl-1,4-benzoquinone (527-61-7) + 3,3',5,5'-tetramethyl-4,4'-diphenoquinone

Conditions	Yield
With C34H22Cl4CoCu2N10O4(1-)*C8H20N(1+); oxygen; sodium hydroxide In methanol at 25℃; for 6h;	A 77% B 10%
With vanadium(V); acetic acid In water at 25℃; Rate constant; Product distribution; Mechanism; effect of substrate, oxidant concentration, acidity, further temperature, solvent;

N-acetyl-3,5-dimethyl-1,4-benzoquinone imine (74827-88-6) → 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With water In acetone for 6h; Heating;	76%

2.6-dimethylphenol (576-26-1) → 3,3',5,5'-tetramethyldiphenoquinone (4906-22-3) + 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With cobalt(III) acetate In acetic acid at 70℃; for 5.5h;	A 75% B 23%
With oxygen; NPV6Mo6/C In acetic acid at 60℃; under 760 Torr; for 5h;	A 52% B 29%
With 2(O2) (1); oxygen In chloroform at 25℃; under 735.5 Torr; for 2h; Rate constant; Product distribution; Mechanism; other phenols and catechol;

2.6-dimethylphenol (576-26-1) → 2,6-dimethyl-1,4-benzoquinone (527-61-7) + 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl (2417-04-1) + 3,3',5,5'-tetramethyl-4,4'-diphenoquinone

Conditions	Yield
With C34H24Cl4Cu2FeN10O4(1-)*C8H20N(1+); oxygen; sodium hydroxide In methanol at 25℃; for 6h;	A 73% B 12% C 15%

2,6-dimethyl-cyclohex-3-ene-1,2-diol (187873-55-8) → 1,4-dihydroxy-2,6-dimethylbenzene (654-42-2) + 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; for 1h;	A 71% B 6%

4-(hydroxymethyl)-2,6-dimethylphenol (4397-14-2) → 4-hydroxy-3,5-dimethylbenzaldehyde (2233-18-3) + 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With oxygen; amine>cobalt In dichloromethane under 2585.7 Torr; for 20h; Ambient temperature;	A n/a B 70%
With K10 montmorillonite; water; dihydrogen peroxide In tetrachloromethane at 22℃; for 2h; Oxidation;	A 3 % Chromat. B 57 % Chromat.

Mesitol (527-60-6) → 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With oxygen; horseradish peroxidase pH=7; Oxidation; electrolysis after 8 F;	70%
Multi-step reaction with 2 steps 1: 5 percent Chromat. / H2O2; K10 montmorillonite; H2O / CCl4 / 2 h / 22 °C 2: 59 percent Chromat. / H2O2; K10 montmorillonite; H2O / CCl4 / 2 h / 22 °C View Scheme
Multi-step reaction with 2 steps 1: 12 percent Chromat. / H2O2; K10 montmorillonite; H2O / CCl4 / 2 h / 22 °C 2: 5 percent Chromat. / H2O2; K10 montmorillonite; H2O / CCl4 / 2 h / 22 °C View Scheme

4-hydroxy-3,5-dimethylbenzaldehyde (2233-18-3) → 1,4-dihydroxy-2,6-dimethylbenzene (654-42-2) + 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine; oxygen; sodium hydrogencarbonate In water; acetonitrile at 20℃; for 3h; Dakin Phenol Oxidation;	A 23% B 65%

Mesitol (527-60-6) → 2,6-dimethyl-1,4-benzoquinone (527-61-7) + 3,3',5,5'-tetramethyl-4,4'-diphenoquinone

Conditions	Yield
With C34H22Cl4CoCu2N10O4(1-)*C8H20N(1+); oxygen; sodium hydroxide In methanol at 25℃; for 6h;	A 65% B 20%

ethylene glycol (107-21-1) + 3,5-Dimethylphenol (108-68-9) → 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With [bis(acetoxy)iodo]benzene In hexane; ethylene glycol 0 deg C; 0 deg C to RT, 2 h;	63%

4-Amino-3,5-dimethylphenol hydrochloride (14033-85-3) → 2,6-dimethyl-1,4-benzoquinone (527-61-7) + 3,5-dimethyl-4-diazocyclohexa-2,5-dienone

Conditions	Yield
With sulfuric acid; sodium nitrite at 20℃; for 0.333333h;	A n/a B 61%

3,5-dimethylmethoxybenzene (874-63-5) → 2,6-dimethyl-1,4-benzoquinone (527-61-7)

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; urea hydrogen peroxide adduct at 45℃; Sealed tube; Green chemistry;	57%
With tert.-butylhydroperoxide; ruthenium(III) 1,4,7-triazacyclononane-based catalyst In dichloromethane; 1,2-dichloro-ethane at 20℃; for 14h;	15%
With perchloric acid; cerium(IV) perchlorate In acetonitrile at 24.9℃;

m-xylene (108-38-3) → 2,6-dimethyl-1,4-benzoquinone (527-61-7) + 3-methylbenzyl alcohol (587-03-1) + m-tolyl aldehyde (620-23-5)

Conditions	Yield
With cerium(IV) sulphate; sulfuric acid In water at 90℃; for 2h; Kinetics; Mechanism; Rate constant; activation energy, mechanism; other times, other temperatures;	A 7.6% B 16.5% C 55.5%
With cerium (IV) sulfate; sulfuric acid In water at 90℃;	A 7.6% B 16.5% C 55.5%
With cerium (IV) sulfate; sulfuric acid In water at 75℃;	A 17.3% B 14.3% C 48.9%

2,6-dimethylaniline (87-62-7) → 2,6-dimethyl-1,4-benzoquinone (527-61-7) + 2,6-dimethylnitrobenzene (81-20-9)

Conditions	Yield
With tert.-butylhydroperoxide; salcomine In water; 1,2-dichloro-ethane at 23℃; for 1h;	A 27% B 52%

2.6-dimethylphenol (576-26-1) → 2,6-dimethyl-1,4-benzoquinone (527-61-7) + 3,5-dimethyl-2-hydroxy-p-benzoquinone (2913-40-8)

Conditions	Yield
With dihydrogen peroxide; methyltrioxorhenium(VII) In acetic acid at 40℃; for 4h;	A 50% B 5%

2.6-dimethylphenol (576-26-1) → 2,6-dimethyl-1,4-benzoquinone (527-61-7) + 3,5-dimethyl-2-hydroxy-p-benzoquinone (2913-40-8) + 1,7-Dihydroxy-2,6-dioxo-1,3,5,7-tetramethyl-5,8-etheno-1,2,5,6,7,8,4a,8a-octahydro-naphthalin; dimeres 6-Hydroxy-2,6-dimethyl-cyclohexadien-(2,4)-on-(1) (5520-77-4)

Conditions	Yield
With dihydrogen peroxide; methyltrioxorhenium(VII) In acetic acid at 40℃; for 4h;	A 50% B 5% C 23%

methanol (67-56-1) + 2.6-dimethylphenol (576-26-1) → 2,6-dimethyl-1,4-benzoquinone (527-61-7) + (1RS,2RS,3SR,7SR,8SR,10SR)-3,10-dimethoxy-3,5,8,10-tetramethyltricyclo[6.2.2.02,7]dodeca-5,11-diene-4,9-dione

Conditions	Yield
With [bis(acetoxy)iodo]benzene at 20℃; for 1h; Oxidation; cyclization;	A 49% B 16%

methanol (67-56-1) + 2.6-dimethylphenol (576-26-1) → 2,6-dimethyl-1,4-benzoquinone (527-61-7) + 4,4-dimethoxy-2,6-dimethylcyclohexa-2,5-dienone (57197-12-3)

Conditions	Yield
With [bis(acetoxy)iodo]benzene at 20℃; for 1h; Oxidation; Title compound not separated from byproducts;	A n/a B 48%

2,6-dimethyl-1,4-benzoquinone (527-61-7) → 1,4-dihydroxy-2,6-dimethylbenzene (654-42-2)

Conditions	Yield
With sodium dithionite In diethyl ether; water	100%
With sodium dithionite In diethyl ether; water at 20℃;	100%
With isopropyl alcohol; zirconium(IV) oxide for 2h; Heating;	99%

2,6-dimethyl-1,4-benzoquinone (527-61-7) → 2,6-dimethyldihydroquinone (74894-46-5, 74894-47-6)

Conditions	Yield
With hydrogen; Pd on C In methanol under 760.051 Torr;	100%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + cyclopenta-1,3-diene (542-92-7) → (1SR,4RS,4aSR,8aRS)-4a,6-dimethyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione (108299-53-2, 111555-28-3, 111555-29-4)

Conditions	Yield
In dichloromethane for 3h; Diels-Alder Cycloaddition; Reflux;	99%
boron trifluoride diethyl etherate In toluene at -78℃; for 1h;	92%
With iron(III) chloride In neat (no solvent, solid phase) at 20℃; for 1h; Diels-Alder Cycloaddition;	87%
In dichloromethane at 20℃; for 48h; Diels-Alder Cycloaddition; diastereoselective reaction;	70%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + cyclopenta-1,3-diene (542-92-7) → (1S,2R,7S,8R)-2,4-dimethyl-tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione

Conditions	Yield
(S)-oxazaborolidine-aluminum bromide at -78℃; for 2h; Diels-Alder reaction;	99%

3-phenyl-2-butenal (1196-67-4) + 2,6-dimethyl-1,4-benzoquinone (527-61-7) → (S)-3,4a-dimethyl-6-phenyl-4a,5-dihydronaphthalene-1,4-dione (1567408-44-9)

Conditions	Yield
With (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; o-fluoro-benzoic acid In chloroform-d1 at 20℃; for 24h; enantioselective reaction;	99%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + 3-methyl-2-penten-4-yn-1-al (53635-18-0) → C14H12O2 (1567408-52-9)

Conditions	Yield
With (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; o-fluoro-benzoic acid In chloroform-d1 at 20℃; for 24h; enantioselective reaction;	99%

2,6-dimethyl-1,4-benzoquinone (527-61-7) → 1,4-dihydroxy-2,6-dimethylbenzene (654-42-2) + 1,2,4,6-Tetramethyl-cyclohexa-2,5-diene-1,4-diol

Conditions	Yield
With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h;	A 2% B 98%

1-acetoxy-1,3-butadiene (1515-76-0) + 2,6-dimethyl-1,4-benzoquinone (527-61-7) → Acetic acid (1R,4aS,8aS)-4a,6-dimethyl-5,8-dioxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl ester

Conditions	Yield
With boron trifluoride diethyl etherate In toluene at 0℃; for 1.5h; Diels-Alder reaction; Inert atmosphere;	98%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + isoprene (78-79-5) → C13H16O2 (1291100-82-7)

Conditions	Yield
With aluminum tri-bromide; (S)-3,3-diphenyl-1-(o-tolyl)hexahydropyrrolo[1,2-c]-[1,3,2]oxazaborole In 1,1-Dibromoethane; hexane; dichloromethane at -78℃; for 50h; Diels-Alder reaction; optical yield given as %ee; enantioselective reaction;	98%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + (E)-3-methylene-5-styryldihydrofuran-2(3H)-one (106549-54-6) → (E)-4-(3, 5-dimethyl-1,4-benzoquinon-2-yl)-2-methylene-6-phenylhex-5-enoic acid

Conditions	Yield
Stage #1: 2,6-dimethyl-1,4-benzoquinone; (E)-3-methylene-5-styryldihydrofuran-2(3H)-one With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate at 20℃; for 0.5h; Stage #2: With hafnium tetrakis(trifluoromethanesulfonate) at 25℃; for 2h;	98%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + cyclopenta-1,3-diene (542-92-7) → C13H14O2

Conditions	Yield
With (R)-2-(o-methyl)phenyl-CBS-oxazaborolidine; aluminum tri-bromide In dichloromethane; toluene at -78℃; for 2h; Diels-Alder Cycloaddition; Schlenk technique; Inert atmosphere;	98%

trimethylsilyl cyanide (7677-24-9) + 2,6-dimethyl-1,4-benzoquinone (527-61-7) → 4-cyano-3,5-dimethyl-4-trimethylsilyloxycyclohexa-2,5-dien-1-one (42860-69-5)

Conditions	Yield
With triphenylphosphine In dichloromethane for 1h; Heating;	97%
With (K-18-crown-6 ether) cyanide In tetrachloromethane 1.) reflux, 10 h, 2.) room temperature;

2,6-dimethyl-1,4-benzoquinone (527-61-7) → 2,6-dimethyl-2,3-epoxy benzoquinone (99595-89-8)

Conditions	Yield
With HOF* CH3CN at 0℃; for 0.0833333h;	97%

1-methylbuta-1,3-diene (2004-70-8) + 2,6-dimethyl-1,4-benzoquinone (527-61-7) → 2,8,8a-trimethyl-4a,5,8,8a-tetrahydronaphthalene-1,4-dione (51315-87-8)

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; for 0.5h;	96%
With lithium perchlorate In diethyl ether for 0.25h; Ambient temperature;	80%
In benzene
titanium tetrachloride In dichloromethane at -78℃; for 0.5h;

2,6-dimethyl-1,4-benzoquinone (527-61-7) + (2S,4aS,8aR)-1,1,4a-Trimethyl-5-vinyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-2-ol (137325-44-1) → 3β-hydroxy-4,4,16,17-tetramethyl-(14β)-D-homo-18-nor-androsta-9(11),16-diene-15,17a-dione (140375-35-5, 140460-63-5)

Conditions	Yield
In benzene for 20h; Heating;	96%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + (2S,4aS,8aR)-1,1,4a-Trimethyl-5-vinyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-2-ol (137325-44-1) → (4aR,4bR,6aR,8S,10aS,12aS)-8-Hydroxy-2,4a,7,7,10a-pentamethyl-4a,4b,5,6,6a,7,8,9,10,10a,12,12a-dodecahydro-chrysene-1,4-dione

Conditions	Yield
In benzene for 20h; Heating;	96%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + methyl (E)-4,6,7-octatrienoate → 3-((1R,8aR)-4,7,8a-Trimethyl-5,8-dioxo-1,5,8,8a-tetrahydro-naphthalen-1-yl)-propionic acid methyl ester (96302-07-7)

Conditions	Yield
In benzene at 50℃; for 21h;	96%

5-(3,4-dimethoxyphenyl)-oxa-cyclopentan-2-one (14335-78-5) + 2,6-dimethyl-1,4-benzoquinone (527-61-7) → 4-(3,5-dimethyl-1,4-benzoquinon-2-yl)-4-(3,4-dimethoxylphenyl)butyric acid

Conditions	Yield
Stage #1: 5-(3,4-dimethoxyphenyl)-oxa-cyclopentan-2-one; 2,6-dimethyl-1,4-benzoquinone With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate at 20℃; for 0.5h; Stage #2: With hafnium tetrakis(trifluoromethanesulfonate) at 50℃; for 2h;	96%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + 5-(4-bromo-5-chloro-2-thienyl)dihydrofuran-2-one → 4-(3,5-dimethyl-1,4-benzoquinon-2-yl)-4-(4-bromo-5-chlorothiophen-2-yl)butanoic acid

Conditions	Yield
Stage #1: 2,6-dimethyl-1,4-benzoquinone; 5-(4-bromo-5-chloro-2-thienyl)dihydrofuran-2-one With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate at 20℃; for 0.5h; Stage #2: With hafnium tetrakis(trifluoromethanesulfonate) at 50℃; for 2h;	96%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + 3-methylene-5-(4-(methylthio)phenyl)dihydrofuran-2(3H)-one → 4-(3,5-dimethyl-1,4-benzoquinon-2-yl)-2-methylene-4-(4-(methylthio)phenyl)butanoic acid

Conditions	Yield
Stage #1: 2,6-dimethyl-1,4-benzoquinone; 3-methylene-5-(4-(methylthio)phenyl)dihydrofuran-2(3H)-one With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate at 20℃; for 0.5h; Stage #2: With hafnium tetrakis(trifluoromethanesulfonate) at 25℃; for 2h;	96%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + sodium (E)-4,6-heptadienoate (86668-96-4) → C23H26O6 (88710-64-9)

Conditions	Yield
With sodium hydroxide In water for 2h; Ambient temperature;	95%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + ethylene glycol (107-21-1) → 4,4-ethylenedioxy-2,6-dimethyl-2,5-cyclohexadien-1-one (85268-20-8)

Conditions	Yield
With toluene-4-sulfonic acid; trimethyl orthoformate In diethyl ether at 4℃; for 120h;	95%
With toluene-4-sulfonic acid; trimethyl orthoformate at 40℃; for 2h;	90%
With toluene-4-sulfonic acid; trimethyl orthoformate In benzene at 25℃; for 24h;	86%

2-Oxobutyric acid (600-18-0) + 2,6-dimethyl-1,4-benzoquinone (527-61-7) → 1-(3,6-Dihydroxy-2,4-dimethyl-phenyl)-propan-1-one

Conditions	Yield
With ammonium persulfate; silver nitrate In water; acetonitrile at 70℃; for 2h;	95%

bicyclopropylidene (27567-82-4) + 2,6-dimethyl-1,4-benzoquinone (527-61-7) → 6,8-dimethyldispiro[2.0.54.33]dodeca-5,8-diene-7,12-dione (1440547-06-7)

Conditions	Yield
In benzene for 24h; Photolysis; Inert atmosphere; regioselective reaction;	95%

phosphorohydrazidic acid diethyl ester (56183-69-8) + 2,6-dimethyl-1,4-benzoquinone (527-61-7) → N'-(3,5-Dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-phosphorohydrazidic acid diethyl ester

Conditions	Yield
In benzene at 25℃;	94%

Ru(η6-1,3,5-cyclooctatriene)(dimethyl fumarate)2 (223249-01-2) + 2,6-dimethyl-1,4-benzoquinone (527-61-7) → Ru(η6-cyclooctatriene)(2,6-dimethyl-p-benzoquinone) (490012-81-2)

Conditions	Yield
In diethyl ether byproducts: CO2MeCHCHCO2Me; mixt. of Ru-complex, ligand and Et2O was refluxed for 4 h under Ar; filtered, rinsed with Et2O, dried under vac.;	94%

2,6-dimethyl-1,4-benzoquinone (527-61-7) + 2-cinnamyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → (E)-6-cinnamyl-2,6-dimethylcyclohex-2-ene-1,4-dione

Conditions	Yield
In chloroform-d1 at 20℃; for 24h; Inert atmosphere; stereoselective reaction;	94%

Upstream product

• 108-68-9 3,5-Dimethylphenol 
• 7664-93-9 sulfuric acid 
• 88-05-1 2,4,6-trimethylaniline 
• 67-64-1 acetone 
• 75-09-2 dichloromethane 
• 7722-84-1 dihydrogen peroxide 
• 108-38-3 m-xylene 
• 407-25-0 trifluoroacetic anhydride 
• 576-26-1 2.6-dimethylphenol 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 5384-21-4 bis(4-hydroxy-3,5-dimethylphenyl)methane 
• 95-47-6 o-xylene 
• 527-60-6 Mesitol 

Downstream Products

• 41168-76-7 1,3-dimethyl-2,4,5-triacetoxybenzene 
• 146803-78-3 (3,6-dihydroxy-2,4-dimethyl-phenyl)-acetic acid ethyl ester 
• 14033-86-4 2,6-dimethyl-1,4-benzoquinone-4-(2,4,6-trimethil anil) 
• 110182-67-7 3,3'-(4,6-dimethyl-2,5-dioxo-cyclohexa-3,6-diene-1,3-diyldimercapto)-di-propionic acid 
• 66597-09-9 3a,5-dimethyl-3-(2,4,6-trimethyl-phenyl)-3a,7a-dihydro-benzo[d]isoxazole-4,7-dione 
• 108709-09-7 2-(4-Methoxy-phenyl)-4,6-dimethyl-2-thioxo-2λ⁵-benzo[1,3,2]oxathiaphosphol-5-ol 
• 140901-64-0 1,3-Dimethyl-2,5-bis-trimethylsilanyloxy-benzene 
• 140901-60-6 3,3,4,6-Tetramethyl-5-trimethylsilanyloxy-3H-benzofuran-2-one 
• 74598-80-4 2,6-dimethyl-3,5-dimethylthiobenzoquinone 
• 60300-94-9 2,6-Dimethyl-[1,4]benzoquinone; compound with 2,6-dimethyl-benzene-1,4-diol 
• 105381-71-3 N-Cyano-2,6-dimethyl-1,4-benzoquinone-4-imine 
• 98507-15-4 N,N'-Dicyano-2,6-dimethyl-1,4-benzoquinonediimine 
• 131-58-8 2-Methylbenzophenone 
• 73818-08-3 C₂₆H₂₃O₂Si 

Relevant articles and documents

User-friendly synthesis of highly selective and recyclable mesoporous titanium-silicate catalysts for the clean production of substituted p-benzoquinones

Mesoporous titanium-silicates have been prepared following the evaporation-induced self-assembly (EISA) methodology and characterized by elemental analysis, XRD, N2 adsorption, SEM, DRS UV-Vis and Raman techniques. The use of acetylacetone during synthesis allowed the formation of highly dispersed dimeric and/or small oligomeric Ti species, within the mesostructured silica network, to be realized. The materials catalyse oxidation of alkylsubstituted phenols to corresponding p-benzoquinones with 100% selectivity using the green oxidant-30% aqueous hydrogen peroxide. The titanium-silicates prepared by the convenient and versatile EISA-based procedure reveal the true heterogeneous nature of the catalysis and do not suffer from titanium leaching. They show advantages over other types of mesoporous Ti,Si-catalysts, such as TiO2-SiO2 mixed oxides and grafted Ti/SiO2, in terms of the catalyst stability and reusability.

Manganese(III) porphyrin supported onto multi-walled carbon nanotubes for heterogeneous oxidation of synthetic textile dyes and 2,6-dimethylphenol by tert -butyl hydroperoxide

Manganese porphyrin has been supported onto multi-walled carbon nanotubes (Mn(TCPP)OAc@MWCNT) and characterized by powder X-ray diffraction, FT-IR, atomic absorption and UV-vis spectroscopy, field emission scanning electron microscopy (FE-SEM) and also thermogravimetric analysis (TGA). The TGA curve shows that the nanocatalyst was thermally stable up to almost 350 °C. This catalyst was found to be able to oxidize different synthetic textile dyes in aqueous media over a wide pH range at ambient temperature with tert-butyl hydroperoxide (TBHP) as the oxygen source. The influence of some important parameters such as the initial pH of the dye solution, temperature and concentration of the catalyst, the oxidant and the co-catalyst were investigated. Also, the ability of this heterogeneous catalyst to oxidize 2,6-dimethylphenol (with excellent selectivity for quinone (86%)) with TBHP in acetonitrile was evaluated. The separation and recycling of the catalyst is simple and the catalyst can be used several successive cycles without significant decrease in catalytic activity.

Synthetic study of Zoanthamine alkaloids: The C-ring model possessing three consecutive quaternary carbons

Stereo-controlled construction of the C-ring model (4) of zoanthamine alkaloids was achieved via a Sml2-mediated Simmons-Smith reaction.

Organophotocatalytic Aerobic Oxygenation of Phenols in a Visible-Light Continuous-Flow Photoreactor

A mild photocatalytic phenol oxygenation enabled by a continuous-flow photoreactor using visible light and pressurized air is described herein. Products for wide-ranging applications, including the synthesis of vitamins, were obtained in high yields by precisely controlling principal process parameters. The reactor design permits low organophotocatalyst loadings to generate singlet oxygen. It is anticipated that the efficient aerobic phenol oxygenation to benzoquinones and p-quinols contributes to sustainable synthesis.

PHOTOOXIDATION OF PHENOLIC COMPOUNDS

The present invention relates to the photooxidation of phenolic compounds to the respective quinoid compounds using methylene blue as photosensitizer in a solvent mixture of water and alcohols using light of the high wavelength range of the visible spectrum.

PHOTOOXIDATION OF 2,3,5-TRIMETHYLPHENOL

The present invention relates to the photooxidation of 2,3,5-trimethyl- phenol to yield 2,3,5-trimethylbenzoquinone using methylene blue as photo- sensitizer in a solvent mixture of water and alcohols using light of the high wavelength range of the visible spectrum.