78-59-1

Basic information

• Product Name: Isophoron
• Synonyms: 3,5,5-Trimethyl-2-cyclohexen-1-one;3,5,5-Trimethyl-2-cyclohexene-1-one;3,5,5-Trimethyl-2-cyclohexenone;Isoacetophorone;Isoforon;Isophoron;NSC 403657;NSC 4881;a-Isophoron;a-Isophorone;iso-phorone;2-Cyclohexen-1-one,3,5,5-trimethyl-;1,1,3-Trimethyl-3-cyclohexene-5-one;1,5,5-Trimethyl-3-oxocyclohexene;1-Cyclohexen-3-one, 1,5,5-trimethyl-
• CAS NO: 78-59-1
• Molecular Formula: C₉H₁₄O
• Molecular Weight: 140.22274
• EINECS: 201-126-0
• Mol File: 78-59-1.mol
• Article Data: 119

Chemical Properties

• Melting Point: -8℃
• Boiling Point: 215.2 °C at 760 mmHg
• Flash Point: 84.4 °C
• Appearance: light yellow liquid
• Density: 0.905 g/cm³
• Vapor Pressure: 0.15mmHg at 25°C
• Refractive Index: 1.455
• CAS DataBase Reference: Isophoron(CAS DataBase Reference)
• NIST Chemistry Reference: Isophoron(78-59-1)
• EPA Substance Registry System: Isophoron(78-59-1)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R21/22:; R36/37:; R40:
• Safety Statements: S13:; S23:; S36/37/39:; S46:
• Hazardous Substances Data: 78-59-1(Hazardous Substances Data)

Usage

General Description

Isophorone is a colorless liquid ketoamine with a mild, peppermint-like odor. It is primarily used as a solvent in a variety of industries, including coatings, adhesives, pesticides, and personal care products. Isophorone is also used as a chemical intermediate for producing other compounds, such as antioxidants and fragrances. Additionally, it has applications in the manufacturing of pharmaceuticals, as well as in the production of photographic chemicals and inks. Isophorone is considered to be a low-toxicity chemical, but it should still be handled with care and in accordance with proper safety protocols.

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 
• 4839-46-7 3,3-Dimethylglutaric acid 
• 6267-39-6 3-ethoxy-5,5-dimethyl-2-cyclohexen-1-one 
• 28815-33-0 2,6,6-trimethyl-4-oxo-cyclohex-2-enecarboxylic acid 
• 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 
• 10276-21-8 isophorone oxide 

Downstream Products

• 110377-14-5 3-ethyl-2-(3,5,5-trimethyl-cyclohex-2-enylidenemethyl)-benzoxazolium; iodide 
• 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 
• 107100-67-4 3-ethyl-2-thioxo-5-(3,5,5-trimethyl-cyclohex-2-enylidene)-thiazolidin-4-one 
• 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 
• 16609-28-2 1,5,5-trimethyl-3-methylenecyclohex-1-ene 
• 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 articles and documents

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

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