6090-09-1

Basic information

• Product Name: 4-acetyl-1-methyl-1-cyclohexene
• Synonyms: 4-acetyl-1-methyl-1-cyclohexene;1-Methyl-1-cyclohexene-4-yl(methyl) ketone;1-Methyl-4-acetylcyclohexene;4'-Methyl-1',2',3',6'-tetrahydroacetophenone;Methyl(4-methyl-3-cyclohexenyl) ketone;4-Methyl-3-cyclohexen-1-yl methyl ketone;1-(4-Methylcyclohex-3-en-1-yl)ethanone;1-(4-methylcyclohex-3-en-1-yl)ethan-1-one
• CAS NO: 6090-09-1
• Molecular Formula: C₉H₁₄O
• Molecular Weight: 138.21
• Mol File: 6090-09-1.mol
• Article Data: 66

Chemical Properties

• Boiling Point: 189.5±0.0℃ (760 Torr)
• Flash Point: 76.7±0.0℃
• Appearance: /
• Density: 0.9385 g/cm3 (20 ºC)
• Vapor Pressure: 0.568mmHg at 25°C
• Refractive Index: 1.4710 (589.3 nm 20℃)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-acetyl-1-methyl-1-cyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-acetyl-1-methyl-1-cyclohexene(6090-09-1)
• EPA Substance Registry System: 4-acetyl-1-methyl-1-cyclohexene(6090-09-1)

Safety Data

• Hazardous Substances Data: 6090-09-1(Hazardous Substances Data)

Usage

Uses

1-(4-methyl-3-cyclohexen-1-yl)ethanone is an essential oil found in Cedrus atlantica wood and orange peels.

Purification Methods

Purify it by fractionation under reduced pressure in vacuo, and if it is almost pure it can be fractionated at atmospheric pressure, preferably in an inert atmosphere. It forms two semicarbazones one of which is more soluble in *C6H6, and both can be recrystallised from EtOH; the more soluble has m 149o(151o), and the less soluble has m 172-175o(191o). The 4-nitrophenylhydrazone has m 166-167o and the 2,4-dinitrophenylhydrazone has m 114-115o. [Pfau & Plattner Helv Chim Acta 17 129, 142 1934, Adler & Vogt Justus Liebigs Ann Chem 564 109 1949.]

InChI:InChI=1/C9H14O/c1-7-3-5-9(6-4-7)8(2)10/h3,9H,4-6H2,1-2H3

Synthetic route

methyl vinyl ketone (78-94-4) + isoprene (78-79-5) → 5-acetyl-1-methylcyclohexene (41723-53-9) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With zeolite ZSM-5 In dichloromethane Heating;	A 2% B 98%
scandium tris(trifluoromethanesulfonate) In dichloromethane at 0℃; for 13h;	A 6.7% B 91%
With tin (IV) chloride pentahydrate In benzene at 21℃; for 1h; Inert atmosphere;	A n/a B 10%

methyl vinyl ketone (78-94-4) + isoprene (78-79-5) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With C36H47AlClN2O(1+)*C24H12BCl8(1-) In dichloromethane at 20℃; for 12h; Reagent/catalyst; Schlenk technique;	97%
With tris(pentafluoroethyl)difluorophosphorane In dichloromethane at 0 - 25℃; for 21h; Catalytic behavior; Kinetics; Mechanism; Temperature; Time; Diels-Alder Cycloaddition;	93%
With methyltrioxorhenium(VII) In chloroform for 18h; Ambient temperature;	90%

1-(4-methyl-3-cyclohexen-1-yl)ethanol (55511-67-6) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 2h;	93%

(2RS,3SR) 3-diphenylphosphinoyl-2-(4-methylcyclohex-3-enyl)-6-methylhept-5-en-2-ol → (Z)-α-bisabolene (29837-07-8) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 70℃; for 1h;	A 90.7% B n/a

threo-3-diphenylphosphinoyl-2-(4-methylcyclohex-3-enyl)-6-methylhept-5-en-2-ol → (E)‐α‐bisabolene (25532-79-0) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 50℃; for 1h;	A 83.3% B n/a

1-(c-4'-hydroxy-4'-methyl-r-1'-cyclohexyl)ethanone (61187-22-2) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With iodine In toluene for 0.25h; Heating;	81%

C9H15O(1+)*F6Sb(1-) (43103-57-7) → methyl-4 cyclohexenyl-1 methyle cetone (22273-97-8) + 1-(4-methyl-cyclohex-2-enyl)-ethanone (19876-42-7) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
at 40℃; for 1h; Yields of byproduct given. Title compound not separated from byproducts;	A n/a B n/a C 70%

methyl vinyl ketone (78-94-4) + isoprene (78-79-5) → 3-acetyl-1-methylcyclohexene (60048-68-2) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
at 20℃; for 0.666667h; deposition of a mixture of the substrates on the silica gel; reaction with acroleine; acceleration of a Diels-Alder reaction under adsorption conditions;	A n/a B 70%
With tin(IV) chloride In benzene at 5 - 10℃; for 2h;

4-acetyl-1-trimethylsilylmethyl-1-cyclohexene (74043-09-7) → 1-(4-Methylenecyclohexyl)ethanone (17023-58-4) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With potassium fluoride In dimethyl sulfoxide at 120℃; for 12h;	A 10% B 62%
With potassium fluoride In dimethyl sulfoxide at 120℃; for 12h; Yield given;
With potassium fluoride In dimethyl sulfoxide at 120℃; for 12h; Mechanism; Product distribution; Method for preparation of exo-methylenecyclohexanes and cyclohexenes.;

1-acetyl-2-methyl-2-vinylcyclobutane (131510-64-0) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
ethylaluminum dichloride In dichloromethane at 0℃; for 0.5h;	51%

α-4-dimethyl-3-cyclohexene-1-acetaldehyde (29548-14-9) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + 1-(4-methyl-3-cyclohexen-1-yl)ethanol (55511-67-6)

Conditions	Yield
With dihydrogen peroxide; potassium hydroxide In water; dimethyl sulfoxide; isopropyl alcohol at 20 - 80℃; for 3.5h;	A 12% B 46%

p-menthane-2,8,9-triol → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid 1-methyl-4-acetyl-cyclohexen-(1) of unknown optical behaviour;

p-menthane-1,8,9-triol (85734-09-4) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid optically inactive 1-methyl-4-acetyl-cyclohexene-(1);

p-menthane-1,8,9-triol (85734-09-4) → 1-(4-hydroxy-4-methylcyclohexyl)ethan-1-one (5034-20-8) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With sulfate of CrO3

1-(4-hydroxy-4-methyl-cyclohexyl)-ethanone semicarbazone (103985-21-3) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With oxalic acid isomer(ic) mixture;

3-buten-1-yne (689-97-4) + isoprene (78-79-5) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With sulfuric acid; mercury(II) oxide at 45℃; isomer(ic) mixture;

(R)-2-methyl-2-(4-methylcyclohex-3-en-1-yl)-1,3-dioxolane (6090-08-0) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With hydrogenchloride In acetone

limonene. (138-86-3) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With oxygen; uranyl acetate In pyridine Irradiation;
Stage #1: limonene. With cis-[Ru(2,9-Me2phen)2(OH2)2](PF6)2 In acetonitrile at 55℃; for 0.5h; Stage #2: With dihydrogen peroxide In acetonitrile for 8h;
Multi-step reaction with 3 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 2 h / 0 °C / Inert atmosphere 2.1: pyridinium chlorochromate / dichloromethane / 2 h / 0 - 20 °C 3.1: dihydrogen peroxide; potassium hydroxide / dimethyl sulfoxide; isopropyl alcohol; water / 3.5 h / 20 - 80 °C View Scheme
Multi-step reaction with 4 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 2 h / 0 °C / Inert atmosphere 2.1: pyridinium chlorochromate / dichloromethane / 2 h / 0 - 20 °C 3.1: dihydrogen peroxide; potassium hydroxide / dimethyl sulfoxide; isopropyl alcohol; water / 3.5 h / 20 - 80 °C 4.1: pyridinium chlorochromate / dichloromethane / 2 h / 0 - 20 °C View Scheme

4-oxocyclohexanecarboxylic acid (874-61-3) + methyl iodide (74-88-4) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
(i) Li, Et2O, (ii) /BRN= 1635956/; Multistep reaction;

2-phenylsulfinylmethyl-1,3-butadiene (95684-40-5) + methyl vinyl ketone (78-94-4) → 5-acetyl-1-methylcyclohexene (41723-53-9) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

methyl vinyl ketone (78-94-4) + isoprene (78-79-5) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + 1-(5-methylcyclohex-3-enyl)ethanone (55169-94-3)

Conditions	Yield
In toluene at 120℃; for 15h; Yield given;

1-<4-hydroxy-4-methyl-cyclohexyl>-ethanone-(1) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With naphthalene-2-sulfonate at 160 - 180℃; isomer(ic) mixture;

methylmagnesium bromide (75-16-1) + (+-)-4-methyl-cyclohexene-(3)-carbonitrile-(1) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With diethyl ether isomer(ic) mixture;

optically active p-menthanetriol-(2.8.9) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid 1-methyl-4-acetyl-cyclohexen-(1) of unknown optical behaviour;

sulfuric acid (7664-93-9) + p-menthane-1,8,9-triol (85734-09-4) + chromic acid → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + 1-methyl-4-acetyl-cyclohexanol-(1)

(+-)-2-chloro-1-<4-methyl-cyclohex-3-enyl>-ethanone → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
With acetic acid; zinc

(4-Methyl-3-pentenyl) diphenylphosphine oxide (86105-38-6) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) butyllithium / 1.) hexane, THF, 0 deg C, 30 min; 2.) hexane, THF, -78 deg C; 3.) allowed to warm to r.t. during 2 h 2: sodium hydride / dimethylformamide / 1 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1: 1.) butyllithium / 1.) hexane, THF, 0 deg C, 30 min; 2.) hexane, THF, -78 deg C; 3.) allowed to warm to r.t. during 2 h 2: 85 percent potassium hydroxide / dimethylsulfoxide / 1 h / 50 °C View Scheme

trimethyl(2-methylenebut-3-enyl)silane (70901-64-3) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / aluminium chloride / benzene / 3.5 h / 15 - 20 °C / without cat. at 80 deg C, 36 h 2: KF / dimethylsulfoxide / 12 h / 120 °C View Scheme

1-acetyl-2-methylcyclobutene (67223-99-8) → (+-)-4-acetyl-1-methylcyclohexene (6090-09-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) CuBr*Me2S / 1) THF, 40 min, -40 deg C or 30 min, -20 deg C 2) 280 min, -40 deg C 2: 51 percent / EtAlCl2 / CH2Cl2 / 0.5 h / 0 °C View Scheme

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + ortho-anisaldehyde (135-02-4) → (E)-3-(2-methoxyphenyl)-1-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 4h; Claisen-Schmidt Condensation;	98%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + methylmagnesium bromide (75-16-1) → terpineol (98-55-5)

Conditions	Yield
In diethyl ether for 0.5h; Ambient temperature;	97%
With hydrogenchloride 1.) Et2O, 35 deg C, 2 h, 2.) methanol, r.t., 20 min; Yield given. Multistep reaction;

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) → 1-(4-methyl-3-cyclohexen-1-yl)ethanol (55511-67-6)

Conditions	Yield
With aluminium trichloride; diphenylstibane In tetrahydrofuran for 2h; Ambient temperature;	96%
With ethanol; sodium
With C46H45ClN3O2PRu; sodium hydroxide In isopropyl alcohol at 90℃; for 24h; Reagent/catalyst; Glovebox;

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + benzaldehyde (100-52-7) → (E)-1-(4-methylcyclohex-3-en-1-yl)-3-phenylprop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 2h; Reagent/catalyst; Claisen-Schmidt Condensation;	96%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + 4-methyl-benzaldehyde (104-87-0) → (E)-1-(4-methylcyclohex-3-en-1-yl)-3-(p-tolyl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 3h; Claisen-Schmidt Condensation;	95%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + 4-bromo-benzaldehyde (1122-91-4) → (E)-3-(4-bromophenyl)-1-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 2h; Claisen-Schmidt Condensation;	93%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + 4-fluorobenzaldehyde (459-57-4) → (E)-3-(4-fluorophenyl)-1-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 3h; Claisen-Schmidt Condensation;	92%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + 3-nitro-benzaldehyde (99-61-6) → (E)-1-(4-methylcyclohex-3-en-1-yl)-3-(3-nitrophenyl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 4h; Claisen-Schmidt Condensation;	92%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) → 4-acetyl-1,2-epoxy-1-methylcyclohexane (148154-91-0)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane Ambient temperature;	86%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) → 1-(4-methyl-3-cyclohexen-1-yl)-1-ethanone oxime (479683-06-2)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In water; acetonitrile at 20℃; for 3h;	86%

methyl magnesium iodide (917-64-6) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1) → terpineol (98-55-5)

Conditions	Yield
In diethyl ether for 0.25h; Ambient temperature;	85%
With diethyl ether dl-α-terpineol;

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + O-benzylhydoxylamine hydrochloride (2687-43-6) → 1-(4-methylcyclohex-3-en-1-yl)ethanone O-benzyloxime

Conditions	Yield
With sodium acetate In water; acetonitrile at 20℃; for 8h;	82%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) → 4-acetyl-1-methylcyclohexane-1,2-diol

Conditions	Yield
With ruthenium trichloride; sodium periodate In ethyl acetate; acetonitrile for 0.05h;	81%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) → para-methylacetophenone (122-00-9)

Conditions	Yield
With 5 weight% palladium(0) nanoparticles supported on mesoporous natural phosphate In neat (no solvent) for 24h; Reflux;	80%
With sulfuric acid

4-methyl-1,3-pentadiene (926-56-7) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1) → bisabolol (515-69-5, 23089-26-1, 23178-88-3, 25428-43-7, 72059-10-0, 72691-24-8, 76738-75-5, 78148-59-1, 123877-54-3)

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide electroreductive coupling;	80%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + 4-chlorobenzaldehyde (104-88-1) → (E)-3-(4-chlorophenyl)-1-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 4h; Claisen-Schmidt Condensation;	80%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) → C9H14Cl2O

Conditions	Yield
Stage #1: (+-)-4-acetyl-1-methylcyclohexene With iron(III) chloride In dichloromethane; water at 20℃; Stage #2: With sodium hypochlorite In dichloromethane; water at 20℃; for 0.583333h;	80%

ethoxydimethylvinylsilane (5356-83-2) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1) → 2,2,5-Trimethyl-5-(4-methyl-cyclohex-3-enyl)-[1,2]oxasilolane

Conditions	Yield
With tetraethylammonium tosylate In N,N-dimethyl-formamide electrolytic coupling;	79%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + (4-isopropylbenzaldehyde) (122-03-2) → (E)-3-(4-isopropylphenyl)-1-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 2h; Claisen-Schmidt Condensation;	72%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + propargyl magnesium bromide (18295-60-8) → 2-(1-methylcyclohex-1-ene-4-yl)pent-4-yne-2-ol

Conditions	Yield
In diethyl ether for 2h; Ambient temperature;	70%

4-methyleneoxetan-2-one (674-82-8) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1) → 6-methyl-2-(4-methylcyclohex-3-en-1-yl)-1,3-dioxin-4-one (338453-61-5)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 20h; Heating;	70%

(+-)-4-acetyl-1-methylcyclohexene (6090-09-1) + 4-dimethylamino-benzaldehyde (100-10-7) → (E)-3-(4-(dimethylamino)phenyl)-1-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 5h; Claisen-Schmidt Condensation;	68%

Upstream product

• 5989-27-5 D-limonene 
• 4680-24-4 cis-(R)-limonene oxide 
• 78-94-4 methyl vinyl ketone 
• 78-79-5 isoprene 
• 689-97-4 3-buten-1-yne 
• 138-86-3 limonene. 
• 43103-57-7 C₉H₁₅O⁽¹⁺⁾*F₆Sb^(1-) 
• 95684-40-5 2-phenylsulfinylmethyl-1,3-butadiene 
• 75-16-1 methylmagnesium bromide 
• 106-99-0 buta-1,3-diene 
• 203719-53-3 (-)-limonene oxide 
• 5989-54-8 (-)-(S)-limonene 
• 185197-80-2 (4R)-4-acetyl-1,2-epoxy-1-methylcyclohexane 
• 917-54-4 methyllithium 

Downstream Products

• 98-55-5 terpineol 
• 4342-60-3 4-methylcyclohex-3-enecarboxylic acid 
• 622-96-8 4-methylethylbenzene 
• 1879-06-7 4-acetyl-1-methylcyclohexane 
• 5034-20-8 1-(4-hydroxy-4-methylcyclohexyl)ethan-1-one 
• 55511-67-6 1-(4-methyl-3-cyclohexen-1-yl)ethanol 
• 122-00-9 para-methylacetophenone 
• 515-69-5 bisabolol 
• 515-69-5 (+)-(1'R,6S)-α-Bisabolol 
• 515-69-5 α-bisabolol 
• 96160-48-4 2-(4-Methyl-cyclohex-3-enyl)-hex-5-en-2-ol 
• 85895-23-4 4-(4-(phenylthio)-5-methyl-1-oxo-4-hexenyl)-1-methylcyclohexene 
• 86105-39-7 (2R,3R)-3-(Diphenyl-phosphinoyl)-6-methyl-2-(4-methyl-cyclohex-3-enyl)-hept-5-en-2-ol 
• 86105-39-7 (2S,3R)-3-(Diphenyl-phosphinoyl)-6-methyl-2-(4-methyl-cyclohex-3-enyl)-hept-5-en-2-ol 

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