1,3-dimethoxy-5-pentylbenzene
Olivetol
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at -15 - 20℃; for 1.5h; Solvent; Reagent/catalyst; Inert atmosphere; | 95% |
With boron tribromide In dichloromethane at -15 - 20℃; for 1.5h; Inert atmosphere; | 92% |
With boron tribromide In dichloromethane at -15 - 20℃; for 1.5h; Inert atmosphere; | 92% |
methyl 2,4-dihydroxy-6-pentylbenzoate
Olivetol
Conditions | Yield |
---|---|
With water; potassium hydroxide at 50 - 100℃; | 94% |
Olivetol
Conditions | Yield |
---|---|
With sodium; butan-1-ol at 80 - 90℃; for 1h; | 81% |
With hydrogen; palladium on activated charcoal In ethanol Yield given; |
Olivetol
Conditions | Yield |
---|---|
Stage #1: 3,5-diamino-1-pentylbenzene With sulfuric acid; sodium nitrite In dichloromethane at 5℃; Stage #2: With sulfuric acid; sodium sulfate In water for 1h; Reflux; | 78% |
methyl 6-n-pentyl-2-hydroxy-4-oxo-cyclohex-2-ene-1-carboxylate
Olivetol
Conditions | Yield |
---|---|
With bromine In N,N-dimethyl-formamide at 160℃; for 10h; Cooling with ice; | 69.3% |
With bromine In N,N-dimethyl-formamide at 80 - 160℃; | 69.3% |
With bromine In N,N-dimethyl-formamide at 160℃; for 11.5h; Cooling with ice; | 69.3% |
With bromine In N,N-dimethyl-formamide at 160℃; for 10h; Cooling with ice; | 69.3% |
With bromine In N,N-dimethyl-formamide at 80 - 160℃; for 11.5h; Cooling with ice; | 69.3% |
4-Benzenesulfinyl-5-pentyl-cyclohexane-1,3-dione
Olivetol
Conditions | Yield |
---|---|
With calcium carbonate In benzene for 5h; Heating; | 48% |
5-n-amyl-2-bromocyclohex-2-ene-3-ol-1-one
A
4-bromo-5-pentylbenzene-1,3-diol
B
4,6-dibromo-5-pentylbenzene-1,3-diol
C
Olivetol
Conditions | Yield |
---|---|
In diphenylether heating to 155 deg C during 1 h; | A 32% B 10% C 40% |
methanol
olivetoric acid
A
6,8-dihydroxy-3-pentyl-1H-2-benzopyran-1-one
B
Olivetol
Conditions | Yield |
---|---|
at 150 - 200℃; |
formic acid
olivetoric acid
A
6,8-dihydroxy-3-pentyl-1H-2-benzopyran-1-one
B
Olivetol
CBD
pyridine hydrochloride
A
4-methylisopropylbenzene
B
Olivetol
Conditions | Yield |
---|---|
at 210 - 230℃; |
2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester
Olivetol
Conditions | Yield |
---|---|
With sodium hydroxide | |
With sodium hydroxide | |
With sodium hydroxide In water Heating; |
5-n-amyl-2-bromocyclohex-2-ene-3-ol-1-one
Olivetol
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide |
2-Hydroxy-4-oxo-6-pentyl-cyclohex-2-enecarboxylic acid ethyl ester
Olivetol
Conditions | Yield |
---|---|
(i) CuBr2, DME, (ii) (heating in DMF), (iii) aq. NaOH; Multistep reaction; |
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
Non-3-en-2-on
methyl 2-phenylsulfinylacetate
(4S,5S)-4-Benzenesulfinyl-3-hydroxy-5-pentyl-cyclohex-2-enone
(4S,5R)-4-Benzenesulfinyl-3-hydroxy-5-pentyl-cyclohex-2-enone
C
Olivetol
Conditions | Yield |
---|---|
With magnesium methanolate In methanol 1.) 1 h, 2.) room temperature, 2 d; Yield given. Yields of byproduct given; |
2-hydroxy-4-(2-hydroxy-4-methoxy-6-pentylbenzoyloxy)-6-pentylbenzoic acid
C
Olivetol
Conditions | Yield |
---|---|
at 160℃; for 1h; Product distribution; pyrolysis; rate of decarboxylation; |
methyl 2,6-dihydroxy-4-pentylbenzoate
Olivetol
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water |
Conditions | Yield |
---|---|
With sodium at 140 - 150℃; Erhitzen des Reaktionsprodukts mit KOH auf 250grad; |
2-hydroxy-4-(2-hydroxy-4-methoxy-6-pentylbenzoyloxy)-6-pentylbenzoic acid
A
2-hydroxy-4-methoxy-6-pentylbenzoic acid
B
Olivetol
methanol
olivetoric acid
A
methylammonium carbonate
B
Olivetol
Conditions | Yield |
---|---|
at 150℃; im Rohr; |
formic acid
olivetoric acid
A
methylammonium carbonate
B
Olivetol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: Et3N / tetrahydrofuran / 1 h / 0 - 20 °C 2: 41 percent / Li, naphthalene / tetrahydrofuran / 2 h / -30 - 0 °C 3: 96 percent / Et3N / tetrahydrofuran / 1.08 h / 0 °C 4: 95 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 5: 81 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: PBr3 2: CuI 3: aq. HCl, Py View Scheme |
3,5-dimethoxybenzyl trimethylsilyl ether
Olivetol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 41 percent / Li, naphthalene / tetrahydrofuran / 2 h / -30 - 0 °C 2: 96 percent / Et3N / tetrahydrofuran / 1.08 h / 0 °C 3: 95 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 4: 81 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme |
1,3-dimethoxy-5-(2'-hydroxypentyl)benzene
Olivetol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 96 percent / Et3N / tetrahydrofuran / 1.08 h / 0 °C 2: 95 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 3: 81 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme |
Methanesulfonic acid 1-(3,5-dimethoxy-benzyl)-butyl ester
Olivetol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 2: 81 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 2: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 3: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme |
1-(1-hydroxypentyl)-3,5-dimethoxybenzene
Olivetol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 2: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 89 percent / (COCl)2 / benzene / 2 h, room t., 1 h, reflux 2: 70 percent / NaOAc, H2 / 10percent Pd-C / 2427.2 Torr / 1h, then 60 degC, overnight 3: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 4: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 5: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme | |
Multi-step reaction with 7 steps 4: 28.8 g / fluoroboric acid, sodium nitrite / H2O 5: 7.6 g / warming, distillation 6: 60 percent / lithium chips / 0.5 h 7: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme | |
Multi-step reaction with 4 steps 1: LiAlH4 2: PBr3 3: CuI 4: aq. HCl, Py View Scheme |
3,5-dimethoxybenzoyl chloride
Olivetol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 70 percent / NaOAc, H2 / 10percent Pd-C / 2427.2 Torr / 1h, then 60 degC, overnight 2: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 3: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 4: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme | |
Multi-step reaction with 6 steps 3: 28.8 g / fluoroboric acid, sodium nitrite / H2O 4: 7.6 g / warming, distillation 5: 60 percent / lithium chips / 0.5 h 6: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 60℃; for 4h; | 98% |
With potassium carbonate In acetone at 80℃; for 12.083h; Inert atmosphere; | 98% |
With potassium carbonate In acetone for 4h; Heating; | 89% |
chloromethyl methyl ether
Olivetol
1,3-Bis(methoxymethoxy)-5-pentylbenzene
Conditions | Yield |
---|---|
Stage #1: Olivetol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide at 25℃; Inert atmosphere; | 97% |
Stage #1: Olivetol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere; | 92% |
With N-ethyl-N,N-diisopropylamine In dichloromethane for 16h; Ambient temperature; | 91% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 95% |
2,6-dichloropyridine-3,5-dicarbonitrile
Olivetol
Conditions | Yield |
---|---|
With caesium carbonate In dimethyl sulfoxide at 25℃; for 0.5h; | 93% |
Olivetol
1,3-dihydroxy-2-iodo-5-pentylbenzene
Conditions | Yield |
---|---|
With iodine; sodium hydrogencarbonate In tert-butyl methyl ether; water at 0℃; for 1h; Reagent/catalyst; Solvent; Temperature; | 92% |
With N-iodo-succinimide In methanol at 0℃; for 18h; | 85% |
With 18-crown-6 ether; 3-chloro-benzenecarboperoxoic acid; potassium iodide In dichloromethane 1) room temp., 2) 0 deg C, 15 min.; | 82% |
With 3-chloro-benzenecarboperoxoic acid; potassium iodide In dichloromethane at 0℃; for 0.333333h; | 67% |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 25℃; for 0.25h; | 91% |
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane; N,N-dimethyl-formamide at 0℃; for 7h; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
With caesium carbonate In dimethyl sulfoxide at 120℃; for 18h; | 90% |
N,N-dimethyl-formamide
Olivetol
2,4-dihydroxy-6-pentylbenzaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate at 0 - 20℃; for 8.5h; Vilsmeier-Haack Formylation; Inert atmosphere; regioselective reaction; | 90% |
With trichlorophosphate at 0 - 20℃; for 18h; Vilsmeier-Haack Formylation; | 56% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 170℃; for 1h; Inert atmosphere; Schlenk technique; | 90% |
Conditions | Yield |
---|---|
With caesium carbonate In dimethyl sulfoxide at 120℃; for 18h; | 89% |
Conditions | Yield |
---|---|
With caesium carbonate In dimethyl sulfoxide at 120℃; for 18h; | 88% |
Olivetol
4,6-dibromo-5-pentylbenzene-1,3-diol
Conditions | Yield |
---|---|
With hydrogen bromide In dimethyl sulfoxide; ethyl acetate at 60℃; for 1h; Temperature; Solvent; | 87% |
With bromine In dichloromethane at -15℃; Large scale; | 82% |
With bromine In dichloromethane at -30 - -28℃; for 0.75h; | 73% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 85% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 - 5h; |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; diastereoselective reaction; | 85% |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In glycerol at 145℃; for 5h; | 84% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.5h; Inert atmosphere; diastereoselective reaction; | 84% |
ethyl 2-oxocyclohexane carboxylate
Olivetol
1-hydroxy-3-pentyl-7,8,9,10-tetrahydro-benzo[c]chromen-6-one
Conditions | Yield |
---|---|
Stage #1: ethyl 2-oxocyclohexane carboxylate; Olivetol With trichlorophosphate In toluene at 20℃; for 38h; Stage #2: With water In toluene for 0.5h; | 82% |
With trichlorophosphate; benzene | |
With sulfuric acid |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; diastereoselective reaction; | 82% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.5h; Inert atmosphere; diastereoselective reaction; | 82% |
Geraniol
Olivetol
2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chloroform at 20℃; for 12h; Darkness; | 80% |
With toluene-4-sulfonic acid In chloroform at 20℃; for 12h; Darkness; | 39.9% |
With toluene-4-sulfonic acid In chloroform at 20℃; for 12h; Darkness; | 39.9% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20 - 50℃; | 80% |
1,3,5-trichloro-2,4,6-triazine
Olivetol
5-Pentyl-O,O'-bis(4,6-dichlor-1,3,5-triazin-2-yl)-resorcin
Conditions | Yield |
---|---|
With 2,3,5-trimethyl-pyridine In acetone at 0℃; for 2h; | 79.8% |
(3S,4S)-p-menth-1-ene-3,8-diol
Olivetol
2-[(1S,6S)-6-(1-Hydroxy-1-methyl-ethyl)-3-methyl-cyclohex-2-enyl]-5-pentyl-benzene-1,3-diol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 0℃; for 7h; | 79% |
With toluene-4-sulfonic acid In dichloromethane at 0℃; for 7h; Alkylation; | 79% |
Conditions | Yield |
---|---|
Stage #1: Olivetol With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: 4-Methylbenzyl bromide In acetone at 50℃; Stage #3: pyridine-2-sulfonyl chloride Further stages; | 78% |
Molecular Formula: C16H26N2O2
Molecular Weight: 278.3898 g/mol
EINECS: 207-908-8
Index of Refraction: 1.546
Surface Tension: 43.5 dyne/cm
Melting point: 46-48 °C
Density: 1.068 g/cm3
Flash Point: 148.8 °C
Solubility in water: Slightly soluble
Enthalpy of Vaporization: 57.64 kJ/mol
Boiling Point: 313.3 °C at 760 mmHg
Vapour Pressure: 0.000273 mmHg at 25 °C
Appearance: Off-white crystals or olive to light purple waxy solid
Product Category of Olivetol (CAS NO.500-66-3): API intermediates
Following is the structure of Olivetol (CAS NO.500-66-3):
Hazard Codes:Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S39:Wear eye / face protection.
WGK Germany: 3
RTECS: VH2880000
Olivetol, its cas register number is 500-66-3. It also can be called 3,5-Dihydroxyamylbenzene ; 3-06-00-04695 (Beilstein Handbook Reference) ; 5-Pentyl-1,3-benzenediol ; 5-Pentylresorcinol ; 5-n-Amylresorcinol ; 5-n-Pentylresorcinol. And its IUPAC name is [3-(diethylamino)-2,2-dimethylpropyl] 4-aminobenzoate. Olivetol (CAS NO.500-66-3) is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing and shoes. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. And as soon as to get medical aid. If you have the ingesting of the product : Never give anything by mouth to an unconscious person. Get medical aid. Do not induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
In addition, Olivetol should be stored in a tightly closed container, or stored in a cool, dry, well-ventilated area away from incompatible substances as well as stored protected from light.
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