78-59-1

Usage

Uses

Used in Coatings Industry:
Isophoron is used as a solvent in the coatings industry to dissolve resins and other components, improving the flow and application properties of the coatings.
Used in Adhesives Industry:
In the adhesives industry, Isophoron is used as a solvent to enhance the adhesive's performance by improving its viscosity and bonding strength.
Used in Pesticides Industry:
Isophoron is used as a solvent in the formulation of pesticides, helping to dissolve active ingredients and improve the pesticide's effectiveness.
Used in Personal Care Products Industry:
In the personal care products industry, Isophoron is used as a solvent for ingredients in products such as perfumes, lotions, and creams, providing a pleasant scent and improving the product's texture.
Used in Chemical Intermediates:
Isophoron is used as a chemical intermediate for the production of other compounds, such as antioxidants and fragrances, which are used in various applications across different industries.
Used in Pharmaceutical Manufacturing:
Isophoron is used in the manufacturing of pharmaceuticals, where it serves as a solvent or intermediate in the synthesis of various drugs.
Used in Photographic Chemicals Production:
In the production of photographic chemicals, Isophoron is used as a solvent or intermediate, contributing to the development and processing of photographic films and papers.
Used in Inks Production:
Isophoron is used in the production of inks, where it acts as a solvent to improve the ink's flow and performance on various printing substrates.
Despite its low toxicity, Isophoron should be handled with care and in accordance with proper safety protocols to ensure the safety of workers and the environment.

InChI:InChI=1/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3

Synthetic route

isophorol (470-99-5) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 2,4-dichlorotoluene at 25℃; for 2h; Inert atmosphere;	99%
With pyridine; oxygen; Pd(II)-hydrotalcite In toluene at 80℃; for 3h;	96%
With iodosylbenzene; N,N-ethylenebis(3,5-dichlorosalicylideneiminato)Cr(III)Cl In dichloromethane at 20℃; for 0.666667h;	95%

isophorone oxide (10276-21-8) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With iodine; triphenylphosphine In acetonitrile at 20℃; for 0.25h;	98%
With sodium hydroxide; thiourea dioxide; tetrabutylammomium bromide In tetrahydrofuran at 50℃; for 0.5h;	95%
Stage #1: isophorone oxide With bis(cyclopentadienyl)titanium dichloride; zinc In tetrahydrofuran; acetonitrile for 0.5h; Inert atmosphere; Stage #2: With sodium dihydrogenphosphate; water In tetrahydrofuran; acetonitrile for 0.333333h; Inert atmosphere;	88%

Trimethyl-(3,5,5-trimethyl-cyclohex-2-enyloxy)-silane (136116-41-1) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With chromium(VI) oxide; tert.-butylhydroperoxide; triphenylhydroxysilane In dichloromethane for 17h; Ambient temperature;	98%

6-Benzenesulfinyl-3,5,5-trimethyl-cyclohex-2-enone (107742-85-8) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With ammonium chloride; zinc In tetrahydrofuran at 25℃; for 2h;	98%

3,5,5-Trimethyl-6-phenylsulfanyl-cyclohex-2-enone (107742-84-7) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With ammonium chloride; zinc In tetrahydrofuran at 25℃; for 3h;	95%

3-bromo-5,5-dimethlycyclohex-2-en-1-one (13271-49-3) + methyllithium (917-54-4) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With copper(I) thiophenolate In tetrahydrofuran; diethyl ether at 0℃; for 2.5h;	94%

C9H14OS (99649-02-2, 99649-03-3) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
In chloroform for 25h; Ambient temperature; Irradiation;	90%
With oxygen; methylene blue In chloroform for 24h; Irradiation; Yield given;

(3,5,5-trimethyl-2-cyclohexenyl) ethyl ether (175602-66-1) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 8h; Heating;	90%

(3,5,5-trimethyl-cyclohex-2-enyloxymethyl)-benzene (207395-09-3) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + benzaldehyde (100-52-7)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 8h; Heating;	A 87% B 60%

7-Bromo-9,9-dimethyl-1,4-dioxa-spiro[4.5]dec-7-ene (81036-85-3) + methyl iodide (74-88-4) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	86%
With n-butyllithium 1.) THF, -78 deg C, 2 h, 2.) a) -78 deg C, 1 h, b) RT, 1 h; Yield given. Multistep reaction;

3,5,5-trimethyl-2-<(dimethylthiocarbamoyl)oxy>-2-cyclohexen-1-one (112621-58-6) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With lithium acetate; lithium; acetic acid for 0.25h; Heating;	83%

4-methyl-pent-3-en-2-one (141-79-7) + 2-acetoacetic acid (541-50-4) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
Stage #1: 4-methyl-pent-3-en-2-one; 2-acetoacetic acid With copper(II) bis(trifluoromethanesulfonate) at 20℃; for 12h; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; Reagent/catalyst; Inert atmosphere;	83%

3-allyloxy-1,5,5-trimethyl-cyclohexene → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 12h; Heating;	82%

2-bromoisophorone (117910-76-6) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With boron trifluoride diethyl etherate; sodium iodide In 1,2-dichloro-ethane at 85℃; for 2h;	80%

1'p.methoxyphenyl 1'-cyano 1,3,5,5-tetramethyl 2-cyclohexen 1-ol (77797-05-8) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + p-methoxyphenyl-3' cyano-3' tetramethyl-3,3,5,5 cyclohexanone (77797-11-6) + p-methoxybenzylnitrile (104-47-2)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -70℃; for 0.0833333h; Yield given;	A n/a B 80% C n/a
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -70℃; for 0.0833333h; Yields of byproduct given;	A n/a B 80% C n/a

1-methoxy-3,5,5-trimethyl-2-cyclohexene (50987-46-7) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 4h; Heating;	80%

Diazo-acetic acid 3,5,5-trimethyl-cyclohex-2-enyl ester → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + 2b,4,4-Trimethyl-hexahydro-1-oxa-cyclopropa[cd]inden-2-one

Conditions	Yield
With dirhodium(II) tetrakis(caprolactam) In dichloromethane Heating; Yields of byproduct given;	A n/a B 77%

acetone (67-64-1) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + isopropyl alcohol (67-63-0)

Conditions	Yield
With diphenylgermylenedipotassium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 0.5h; Product distribution; Ambient temperature; KH as reagent;	A 76% B n/a

4-methyl-pent-3-en-2-one (141-79-7) + ethyl acetoacetate (141-97-9) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol for 20h; Heating;	75%

(+/-)-6-acetoxy-3,3,5-trimethylcyclohex-2-en-1-one (19019-49-9) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With 2 In dichloromethane for 0.17h; Ambient temperature;	74%

7,9,9-trimethyl-1,4-dithiaspiro<4,5>dec-6-ene (76793-94-7) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With Oxone; potassium bromide In water; acetonitrile at 20℃; for 1h;	72%
With O-phenyl phosphorodichloridate; N,N-dimethyl-formamide; sodium iodide 1.) acetonitrile, few min, room temp., 2.) 5 h, room temp.; Yield given. Multistep reaction;

1-amino-3,3,5-trimethyl-cyclohexyl hydroperoxide (24829-47-8) + cycloheptanone (502-42-1) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With ammonium acetate In ethanol	70.9%
With ammonium acetate In ethanol	70.9%

trimethyl-3,5,5 cyclohexene-2 thione (30221-55-7) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With oxygen; methylene blue In dichloromethane for 5h; Irradiation;	70%
With oxygen In chloroform Product distribution; Rate constant; Mechanism; Irradiation; investigation of different oxidation methods;

dimedone (126-81-8) + Cp2TiCH2*AlMe2Cl → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
In tetrahydrofuran -40 deg C -> R.T., 90 min;	70%

5,5-dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one (10416-78-1) + methyllithium (917-54-4) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
In diethyl ether for 20h; Ambient temperature;	69%

3,5,5-trimethylcyclohex-3-en-1-one (471-01-2) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With formic acid; dihydrogen peroxide	69%

(2R,3R)-2,3-Bis-(4,5-dimethoxy-2-nitro-phenyl)-7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-ene → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
In acetonitrile Photolysis;	68%

3,5,5-trimethylcyclohex-3-en-1-one (471-01-2) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + 2,6,6-trimethyl-2-cyclohexene-1,4-dione (1125-21-9) + 4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone (14203-59-9)

Conditions	Yield
With Tri-n-octylamine; sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In water at 70℃; for 2h; pH=1.5 - 2; Temperature; Reagent/catalyst;	A 8% B 24% C 67%
With Tri-n-octylamine; sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In water at 90℃; for 2h; pH=1.5 - 2; Catalytic behavior; Reagent/catalyst; Temperature;	A 15% B 46% C 16%
With sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In water at 80℃; for 2h; pH=1.5 - 2; Temperature;	A 22% B 5% C 13%
With oxygen; triethylamine; iron tetrasulfophthalocyanine-TiO2 In dimethyl sulfoxide at 60℃; under 1500.12 Torr; for 24h;	A 10 % Chromat. B 57 % Chromat. C 21 % Chromat.

dimethyl zinc(II) (544-97-8) + (5,5-dimethyl-3-oxo-cyclohex-1-enylsulfanyl)-acetic acid → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
With bis(methyldiphenylphosphine)nickel(II) chloride In tetrahydrofuran at 20℃; for 43h; cross-coupling;	64%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → dihydroisophorone (873-94-9)

Conditions	Yield
With limonene.; Pd-BaSO4 for 0.5h; Heating;	100%
With limonene.; Pd-BaSO4 for 0.5h; Product distribution; Heating; further carrier of catalyst;	100%
With hydrogen; β-cyclodextrin/Pd In water at 25℃; under 15001.2 Torr; for 2h;	100%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + ethyl 3-trimethylsiloxy-2-butenoate (13257-83-5) → 1,3,3,8-Tetramethyl-5-oxo-8-trimethylsilanyloxy-bicyclo[4.2.0]octane-7-carboxylic acid ethyl ester (82084-31-9)

Conditions	Yield
In benzene for 24h; Ambient temperature; Irradiation;	100%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → 2-chloroisophorone (17304-82-4)

Conditions	Yield
With Oxone; sodium chloride In tetrachloromethane; water at 0 - 25℃;	100%
With pyridine; sulfuryl dichloride
With fluorosulfonylchloride
With calcium hypochlorite; Methamphetamin In dichloromethane; water for 3h;
With chlorine 1.) CH2Cl2, -3 - 8 deg C; 2.) CCl4, DMF, 75-80 deg C, 30 min; Yield given. Multistep reaction;

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + acetic acid (64-19-7) → (+/-)-6-acetoxy-3,3,5-trimethylcyclohex-2-en-1-one (19019-49-9)

Conditions	Yield
Stage #1: acetic acid With potassium permanganate; acetic anhydride In benzene at 85℃; for 0.5h; Stage #2: 3,5,5-Trimethylcyclohex-2-en-1-one In benzene at 85℃; Temperature;	100%
With potassium permanganate In benzene Heating;	86%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → (R)-3,3,5-trimethylcyclohexanone (33496-82-1)

Conditions	Yield
With dodecacarbonyltetrarhodium(0); (S)-bis(4-(tert-butyl)phenyl)methyl-3-(1-acetyl-1H-indol-3-yl)-2-aminopropanoate; hydrogen; triphenylphosphine In toluene at 90℃; under 60006 Torr; for 10h; Autoclave;	99.8%
Stage #1: 3,5,5-Trimethylcyclohex-2-en-1-one With polymethylhydrosiloxane; copper(l) chloride; sodium t-butanolate; (R)-(2,3-methylenedioxy-6-(4-MeO-3,5-tBu2-C6H2)2P-C6H2)2 In tetrahydrofuran at -35℃; for 1h; Stage #2: In tetrahydrofuran Alkaline hydrolysis;	95%
With (R)-(-)-DTBM-SEGPHOS; sodium phenoxide; poly(methylhydrosiloxane); copper carbide In toluene; tert-butyl alcohol at 20℃; for 3h; ultrasonication;	86%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → 3,5,5-trimethyl-2-cyclohexen-1-ol

Conditions	Yield
With (acetylacetonato)dicarbonylrhodium (l); L-valine; hydrogen; Oxalsaeurebis<(3R,4R)-3,4-bis(diphenylphosphino)pyrrolidid> at 25℃; under 45004.5 Torr; for 36h; Autoclave;	99.1%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + tetraallyl tin (7393-43-3) → 1-allyl-3,5,5-trimethyl-2-cyclohexen-1-ol (21436-26-0)

Conditions	Yield
With n-butyllithium; neodymium(III) chloride In tetrahydrofuran; hexane for 1h; Ambient temperature;	99%
With n-butyllithium; neodymium(III) chloride 1.) hexane, THF, RT, 1 h, 2.) hexane, THF, 0 deg C, 1 h; Yield given. Multistep reaction;

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + manganese triacetate (638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3) → (+/-)-6-acetoxy-3,3,5-trimethylcyclohex-2-en-1-one (19019-49-9)

Conditions	Yield
With acetic acid In benzene for 7h; Heating;	99%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + 3-chloro-benzonitrile (766-84-7) → 3-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)benzonitrile

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	99%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + 3-chlorobenzoic acid tert-butyl ester (16537-17-0) → tert-butyl 3-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)benzoate

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	99%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + 6-chloro-2-methoxypyridine (17228-64-7) → 3-((6-methoxypyridin-2-yl)methyl)-5,5-dimethylcyclohex-2-enone

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	99%

2-chloro-3-methylthiophene (14345-97-2) + 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → 5,5-dimethyl-3-((3-methylthiophen-2-yl)methyl)cyclohex-2-enone

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	99%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + 1-chloro-3-methoxy-benzene (2845-89-8) → 3-(3-methoxybenzyl)-5,5-dimethylcyclohex-2-enone

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	99%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → 3,5,5-trimethylcyclohex-3-en-1-one (471-01-2)

Conditions	Yield
at 206℃; under 750.075 Torr; for 48h; Catalytic behavior; Pressure; Temperature; Inert atmosphere;	98.3%
at 210 - 240℃; under 375.038 Torr; Pressure; Molecular sieve;	91.72%
With methylmagnesium bromide; acetic acid Isomerization;	82%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → isophorone oxide (10276-21-8)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In ethanol at 30 - 35℃; for 1h;	98%
With 3,3-dimethyldioxirane In dichloromethane; acetone at 20℃; for 24h;	90%
With Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate In acetonitrile at 0 - 1℃; for 1.5h;	90%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → isophorol (470-99-5)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 6h;	98%
With lithium aluminium tetrahydride In diethyl ether at -20℃;	95%
With Co-doped ammonia borane In methanol at 20℃; for 2h; Reagent/catalyst; chemoselective reaction;	95%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → 2-hydroxy-4,4,6-trimethylcyclohexa-2,5-diene-1-one (28750-52-9)

Conditions	Yield
With 18-crown-6 ether In benzene for 2h; Ambient temperature;	98%
With KO2; 18-crown-6 ether In benzene for 2h; Ambient temperature;
With potassium superoxide In benzene

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → 3,5,5-trimethyl-3-vinylcyclohexanone (27749-07-1)

Conditions	Yield
With boron trifluoride diethyl etherate; vinyl(2-thienyl)Cu(CN)Li2 In tetrahydrofuran; diethyl ether at -78℃; for 1h; Product distribution; Mechanism; effect of BF3*Et2O and other Lewis Acids;	98%
With (CH2=C)2Cu(CN)Li2 In diethyl ether at -50℃; for 2.5h; Product distribution; other solvents;	98%
With 2-ThNa*CuCN*C2H3Li Product distribution; with and without BF3*Et2O additive;
Multi-step reaction with 2 steps 1: 1) CuCN, TMEDA / 1) THF, -78 deg C, 20 min, 2) THF, 30 min 2: 1 M HCl View Scheme

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + 2-ThLi*CuCN*C2H3Li → 3,5,5-trimethyl-3-vinylcyclohexanone (27749-07-1)

Conditions	Yield
With boron trifluoride diethyl etherate at -78℃; for 3h;	98%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + vinyl-(2-thienyl)Cu(CN)Li2 → 3,5,5-trimethyl-3-vinylcyclohexanone (27749-07-1)

Conditions	Yield
With boron trifluoride diethyl etherate In tetrahydrofuran; diethyl ether at -78℃; for 1h;	98%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + 4-chloro-1,2-difluorobenzene (696-02-6) → 3-(3,4-difluorobenzyl)-5,5-dimethylcyclohex-2-enone

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	98%

4-Cyanochlorobenzene (623-03-0) + 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → 4-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)benzonitrile

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	98%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + 2-methylchlorobenzene (95-49-8) → 5,5-dimethyl-3-(2-methylbenzyl)cyclohex-2-enone

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	98%

chloro-trimethyl-silane (75-77-4) + 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + vinyl magnesium bromide (1826-67-1) → trimethyl-(3,5,5-trimethyl-3-vinylcyclohex-1-enyloxy)silane (108612-90-4)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; magnesium; copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -70℃; for 1.5h;	97%
With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -78℃;	97%
Stage #1: vinyl magnesium bromide With copper(l) iodide In tetrahydrofuran at -10℃; for 0.0333333h; Metallation; Stage #2: 3,5,5-Trimethylcyclohex-2-en-1-one In tetrahydrofuran at -78℃; for 0.5h; Addition; Stage #3: chloro-trimethyl-silane With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; triethylamine In tetrahydrofuran at -78 - 20℃; silylation;	93%
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃;	80%
With N,N,N,N,-tetramethylethylenediamine 1) THF, -78 deg C, 20 min, 2) THF, 30 min; Multistep reaction;

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + C23H35NO3 (1160424-45-2) → C32H47NO3

Conditions	Yield
With sodium ethanolate In ethanol at 120℃; for 0.5h; Knoevenagel Condensation; Microwave irradiation;	97%
With ethanol; sodium at 85℃; for 1h; pH=13; Temperature; Microwave irradiation;	97%
With sodium ethanolate In ethanol at 80℃; for 8h; pH=13;	65%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + di-isopropyl azodicarboxylate (2446-83-5) → diisopropyl 1-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)hydrazine-1,2-dicarboxylate

Conditions	Yield
Stage #1: 3,5,5-Trimethylcyclohex-2-en-1-one With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 1.66667h; Sealed tube; Inert atmosphere; Stage #2: di-isopropyl azodicarboxylate In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere; Sealed tube; regioselective reaction;	97%

Upstream product

• 64-18-6 formic acid 
• 3212-51-9 5,5-Dimethyl-3-(2'-methyl-1'-propen-1'-yl)-2-cyclohexen-1-on 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 5857-71-6 6-hydroxy-2,6-dimethyl-hept-2-en-4-one 
• 4839-46-7 3,3-Dimethylglutaric acid 
• 6267-39-6 3-ethoxy-5,5-dimethyl-2-cyclohexen-1-one 
• 62000-45-7 1-chloro-5,5-dimethyl-3-methylene-cyclohexene 
• 65253-28-3 (Z)-3-ethoxy-5,5-dimethyl-2-cyclohexenylidene acetonitrile 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 141-97-9 ethyl acetoacetate 
• 67-64-1 acetone 
• 1066-26-8 sodium acetylide 
• 14593-46-5 sodium tert-pentoxide 
• 71-43-2 benzene 

Downstream Products

• 110489-34-4 3-ethyl-2-(3,5,5-trimethyl-cyclohex-2-enylidenemethyl)-benzoselenazolium; iodide 
• 60417-86-9 2,3,5,5-tetramethylcyclohex-2-en-1-one 
• 16609-28-2 1,5,5-trimethyl-3-methylenecyclohex-1-ene 
• 107100-67-4 3-ethyl-2-thioxo-5-(3,5,5-trimethyl-cyclohex-2-enylidene)-thiazolidin-4-one 
• 103034-62-4 3,5,5,3',5',5'-hexamethyl-6,6'-hexanediyl-bis-cyclohex-2-enone 
• 31608-30-7 acetic acid-(3,3,5-trimethyl-cyclohexa-1,5-dienyl ester) 
• 34685-93-3 3-ethyl-2-(3,5,5-trimethyl-cyclohex-2-enylidenemethyl)-benzothiazolium; iodide 
• 14376-79-5 3,3,5,5-tetramethylcyclohexanone 
• 471-01-2 3,5,5-trimethylcyclohex-3-en-1-one 
• 3264-17-3 1,5,5,1',5',4'-hexamethyl-bicyclohexyl-3,3'-dione 
• 94925-94-7 3-Hydroxy-1,3,5,5-Tetramethylcyclohexen 
• 75232-18-7 3-isopropyl-3,5,5-trimethyl-cyclohexanone 
• 108540-60-9 1,5,5-trimethyl-3-(ξ-propenyl)-cyclohexa-1,3-diene 
• 122364-54-9 3,5,5-trimethyl-1-propyl-cyclohex-2-enol 

Relevant academic research and scientific papers

Oxidized caesium/nanoporous carbon materials: Solid-base catalysts with highly-dispersed active sites

By vapor depositing Cs metal on nanoporous carbon materials and then oxidizing, a solid-base catalyst is produced that is quite active for the aldol condensation of acetone to isophorone.

Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide

Chlorine is the 20th most abundant element on the earth compared to bromine, iodine, and fluorine, a sulfonimide reagent, N-chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI) was identified as a mild and selective oxidant. Without activation, the reagent was proved to oxidize primary and secondary alcohols as well as their symmetrical and mixed ethers to corresponding aldehydes and ketones. With recoverable PS-TEMPO catalyst, selective oxidation over chlorination of primary and secondary alcohols and their ethers with electron-donating substituents was achieved. The reagent precursor of NCBSI was recovered quantitatively and can be reused for synthesizing NCBSI.

Zwitterion-induced organic-metal hybrid catalysis in aerobic oxidation

In many metal catalyses, the traditional strategy of removing chloride ions is to add silver salts via anion exchange to obtain highly active catalysts. Herein, we reported an alternative strategy of removing chloride anions from ruthenium trichloride using an organic [P+-N-] zwitterionic compound via multiple hydrogen bond interactions. The resultant organic-metal hybrid catalytic system has successfully been applied to the aerobic oxidation of alcohols, tetrahydroquinolines, and indolines under mild conditions. The performance of zwitterion is far superior to that of many other common Lewis bases or Br?nsted bases. Mechanistic studies revealed that the zwitterion triggers the dissociation of chloride from ruthenium trichloride via nonclassical hydrogen bond interaction. Preliminary studies show that the zwitterion is applicable to catalytic transfer semi-hydrogenation.

Aldol Condensation Versus Superbase-Catalyzed Addition of Ketones to Acetylenes: A Quantum-Chemical and Experimental Study

The mechanism of aldol condensation of ketones in KOH/DMSO superbasic media has been investigated using the B2PLYP(D2)/6-311+G**//B3LYP/6-31+G? quantum-chemical approach. It is found that the interaction of three ketone molecules resulting in the formation of the cyclohex-2-enone structure [isophorone or 3,5-dicyclohexyl-5-methylspiro(5.5)undec-2-en-1-one] is thermodynamically more favorable than the interaction of two, three, or four molecules of ketone, resulting in the formation of linear products of the condensation. The formation of the condensation products with the isophorone skeleton can significantly hinder the cascade reactions of ketones with acetylenes [to afford 6,8-dioxabicyclo(3.2.1)octanes or acylcyclopentenols] promoted by superbases. In particular, the kinetically more preferable reactions of autovinylation of 2-methyl-3-butyn-2-ol and autocondensation of acetone are the reasons why interaction of acetone with acetylene does not lead to the products of the cascade assemblies. The predominant formation of the products of these side reactions is confirmed experimentally.

Base-free oxidation of alcohols enabled by nickel(ii)-catalyzed transfer dehydrogenation

An efficient nickel(ii)-catalyzed transfer dehydrogenation oxidation of alcohols is reported that relies on cyclohexanone as the formal oxidant and does not require the use of an external base. The synthetic utility of this protocol is demonstratedviathe facile oxidation of structurally complicated natural products.

Nickel-catalyzed deoxygenation of oxiranes: Conversion of epoxides to alkenes

Deoxygenation of epoxides takes place under the catalysis of nickel in the presence of diethylzinc as a deoxygenation agent to yield alkenes. Epoxides with a wide variety of substitution patterns are deoxygenated in this catalytic system to give terminal, 1,1-disubstituted, 1,2-disubstituted, trisubstituted, and tetrasubstituted alkenes in high yields. Reactions of 1,2-disubstituted epoxides we examined proceeded in an E-stereoselective manner. High compatibility with other functional groups through this transformation was also observed.

Method for preparing triacetone amine

An improved method is used for preparing triacetone amine while recycling the by-products. This involves treating the crude product from triacetone amine preparation, which leads to an increase in the content of compounds which react readily with ammonia. This method enables efficient recycling of the by-products formed in the synthesis of triacetone amine.

Transfer-dehydrogenation of secondary alcohols catalyzed by manganese NNN-pincer complexes

Novel catalytic systems based on pentacarbonylmanganese bromide and stable NNN-pincer ligands are presented for the transfer-dehydrogenation of secondary alcohols to give the corresponding ketones in good to excellent isolated yields. Best results are obtained using di-picolylamine derivatives as ligands and acetone as an inexpensive hydrogen acceptor. Besides high activity for benzylic substrates, aliphatic alcohols, as well as steroid derivatives, are readily oxidized in the presence of the optimal phosphorus-free catalyst.

Iron–PNP-Pincer-Catalyzed Transfer Dehydrogenation of Secondary Alcohols

The well-defined iron PNP pincer complex catalyst [Fe(H)(BH4)(CO)(HN{CH2CH2P(iPr)2}2] was used for the catalytic dehydrogenation of secondary alcohols to give the corresponding ketones. Using acetone as inexpensive hydrogen acceptor enables the oxidation with good to excellent yields. DFT computations indicate an outer-sphere mechanism and support the importance of an acceptor to achieve this transformation under milder conditions.

CATALYTIC OXIDATION OF 3,5,5-TRIMETHYLCYCLOHEXA-3-ENE-1-ONE (?-ISOPHORONE) WITH HYDROGEN PEROXIDE TO AFFORD 2,6,6-TRIMETHYL-2-CYCLOHEXENE-1,4-DIONE (KETO-ISOPHORONE)

The present invention provides a novel process for producing 2,6,6-trimethyl-2-cyclohexene-1,4-dione (keto-isophorone) by catalytic oxidation of 3,5,5-trimethylcyclohexa-3-ene-1-one (β-isophorone) with hydrogen peroxide as the oxidant. In particular, the novel process includes phase transfer reagent in a biphasic system including an organic phase and an aqueous phase wherein the biphasic system includes 1) a tungsten polyoxyometallate as catalyst and hydrogen peroxide, and/or 2) a mixture of a) a mineral acid, b) hydrogen peroxide, and c) a metal tungstate.