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3,7,11,15-tetramethyl-1-hexadecyne-3-ol
A
dihydroisophytol
B
isophytol
Conditions | Yield |
---|---|
With hydrogen; silica gel In ethanol at 69.9℃; under 3750.3 Torr; | A 99.4% B 0.6% |
With hydrogen; silica gel In ethanol at 29.9℃; under 3750.3 Torr; | A 48% B 52% |
With hydrogen; Ni(C17H35COO)2; triethylaluminum In toluene at 40℃; Kinetics; Object of study: selectivity; | |
With quinoline; hydrogen; Lindlar catalyst with MnCl2 doping salt In n-heptane at 25℃; under 735 - 738 Torr; Product distribution; without doping salt; | |
With hydrogen; ShPAK-0.5 modified by Zn(OAc)2 + NH3 In isopropyl alcohol at 50℃; under 735.508 - 1471.02 Torr; for 5h; |
3-Bromomethyl-2-methyl-2-(4,8,12-trimethyl-tridecyl)-oxirane
isophytol
Conditions | Yield |
---|---|
With copper(l) iodide; zinc In ethanol sonication; | 94% |
3-Iodomethyl-2-methyl-2-(4,8,12-trimethyl-tridecyl)-oxirane
isophytol
Conditions | Yield |
---|---|
With copper(l) iodide; zinc In ethanol sonication; | 94% |
3,7,11,15-tetramethyl-1-hexadecyne-3-ol
isophytol
Conditions | Yield |
---|---|
With 2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol; hydrogen; Pd/ZnO/sintered metal fibers (SMF) catalyst at 80℃; under 3000.3 Torr; for 4.5h; Product distribution / selectivity; | 93.7% |
With hydrogen; 2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol at 80℃; under 1500.15 Torr; for 4h; Product distribution / selectivity; Autoclave; | 89.6% |
With methanol; palladium on activated charcoal; hydrogen |
Conditions | Yield |
---|---|
Stage #1: Vinyl bromide With magnesium In tetrahydrofuran Metallation; Stage #2: 6,10,14-Trimethyl-2-pentadecanon In tetrahydrofuran at 0 - 20℃; for 14h; Grignard reaction; | 90% |
Conditions | Yield |
---|---|
In tetrahydrofuran Grignard reaction; | 85% |
In tert-butyl methyl ether at 0 - 5℃; for 2h; | 85% |
at 0 - 5℃; for 2h; Inert atmosphere; | 42.6 g |
isophytol
Conditions | Yield |
---|---|
With naphthalen-1-yl-lithium In tetrahydrofuran at -25℃; for 0.166667h; | 84% |
Conditions | Yield |
---|---|
In tetrahydrofuran 1.) r.t. 2.) reflux 2 h; | 80% |
[3-methyl-3-(4,8,12-trimethyl-tridecyl)-oxiranyl]-methanol
A
neophytadiene
B
isophytol
C
3,7,11,15-tetramethyl-2-hexadecen-1-ol
Conditions | Yield |
---|---|
With methyltrioxorhenium(VII); triphenylphosphine In toluene for 3h; Reflux; | A 7.4% B n/a C n/a |
5-benzenesulfonyl-3,7,11,15-tetramethyl-hexadec-1-en-3-ol
isophytol
Conditions | Yield |
---|---|
With sodium amalgam In methanol |
isophytol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether |
Conditions | Yield |
---|---|
Hydrogenation; |
2,2-Ethylenedioxy-6,10,14-trimethylpentadecane
isophytol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / 5 percent aq. H2SO4 / acetone / 10 h / 20 °C 2: 85 percent / tetrahydrofuran View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / H2 / Pd/C 2: 85 percent / tetrahydrofuran View Scheme |
isophytol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 92 percent / H2 / 5 percent Pd/C / ethyl acetate / 5 h / 20 °C 2: 85 percent / 5 percent aq. H2SO4 / acetone / 10 h / 20 °C 3: 85 percent / tetrahydrofuran View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 0.6 g / H2 / 10 percent Pd/C / ethanol / 72 h / 20 °C 2.1: Mg / tetrahydrofuran 2.2: 90 percent / tetrahydrofuran / 14 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: H2 / Pd-C View Scheme | |
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / isopropyl alcohol / 3 h / 100 °C 2: 2 h / 0 - 5 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: hydrogen; palladium 10% on activated carbon / ethanol / 24 h / 20 °C / 1520.1 Torr 2: tert-butyl methyl ether / 2 h / 0 - 5 °C View Scheme |
trans,trans,trans-1,5,9-trimethyl-1,5,9-cyclododecatriene
isophytol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: O3; O2 / cyclohexane; methanol / 5 °C 1.2: 53 percent / H2 / Pd/CaCO3/PbO 2.1: t-BuOK / tetrahydrofuran / 2.5 h / -40 - 25 °C 2.2: 57 percent / tetrahydrofuran / 2 h / -78 - 25 °C 3.1: 0.6 g / H2 / 10 percent Pd/C / ethanol / 72 h / 20 °C 4.1: Mg / tetrahydrofuran 4.2: 90 percent / tetrahydrofuran / 14 h / 0 - 20 °C View Scheme |
4,8-Dimethyl-1,12-dioxotrideca-4E,8E-diene
isophytol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: t-BuOK / tetrahydrofuran / 2.5 h / -40 - 25 °C 1.2: 57 percent / tetrahydrofuran / 2 h / -78 - 25 °C 2.1: 0.6 g / H2 / 10 percent Pd/C / ethanol / 72 h / 20 °C 3.1: Mg / tetrahydrofuran 3.2: 90 percent / tetrahydrofuran / 14 h / 0 - 20 °C View Scheme |
isophytol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine 2: LiAlH4 / diethyl ether View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 2: 70 percent / benzene / 10 h / Heating 3: 60 percent / KOH / methanol; H2O / 4 h / Heating 4: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme | |
Multi-step reaction with 4 steps 1: PBr3, Py 2: dimethylformamide 3: nBuLi / tetrahydrofuran 4: Na-Hg / methanol View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 1) NaH / tetrahydrofuran / 1.) r. t., 6 h 3.) 50-55 deg C, 4 h 2: 90 percent / H2 / Pt/C / ethanol / 3102.9 Torr / Ambient temperature 3: 65 percent / 1) LAH / diethyl ether / 1) kept overnight 2) 2 h reflux 4: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 5: 70 percent / benzene / 10 h / Heating 6: 60 percent / KOH / methanol; H2O / 4 h / Heating 7: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme | |
Multi-step reaction with 3 steps 1: tert-butyl methyl ether / 6 h / 0 °C / Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / ethanol / 24 h / 20 °C / 1520.1 Torr 3: tert-butyl methyl ether / 2 h / 0 - 5 °C View Scheme |
ethyl 3,7,11-trimethyldodecanoate
isophytol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 65 percent / 1) LAH / diethyl ether / 1) kept overnight 2) 2 h reflux 2: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 3: 70 percent / benzene / 10 h / Heating 4: 60 percent / KOH / methanol; H2O / 4 h / Heating 5: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme |
ethyl 2-acetyl-5,9,13-trimethyltetradecanoate
isophytol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 60 percent / KOH / methanol; H2O / 4 h / Heating 2: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme |
(2Z,6E)-ethyl 3,7,11-trimethyldodeca-2,6,10-trienoate
isophytol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 90 percent / H2 / Pt/C / ethanol / 3102.9 Torr / Ambient temperature 2: 65 percent / 1) LAH / diethyl ether / 1) kept overnight 2) 2 h reflux 3: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 4: 70 percent / benzene / 10 h / Heating 5: 60 percent / KOH / methanol; H2O / 4 h / Heating 6: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme |
1-mesyloxy-3,7,11-trimethyldodecane
isophytol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 70 percent / benzene / 10 h / Heating 2: 60 percent / KOH / methanol; H2O / 4 h / Heating 3: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme |
2-<2-(phenylthio)ethyl>prop-2-en-1-ol
isophytol
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: Hg(OAc)2 / 24 h / Heating 2: xylene / 3 h / 140 °C 3: 62 percent / tetrahydrofuran / 2 h / Heating 4: 79 percent / t-BuOOH, V2O5 5: n-BuLi / tetrahydrofuran / 1 h / -78 °C 6: PdCl2, CuCl, O2 / dimethylformamide; H2O / 12 h / Ambient temperature 7: 1.) DBU, CH2Cl2, reflux, 1 hr 2.) Pd/C, H2, EtOH View Scheme |
(3-Vinyloxymethyl-but-3-enylsulfanyl)-benzene
isophytol
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: xylene / 3 h / 140 °C 2: 62 percent / tetrahydrofuran / 2 h / Heating 3: 79 percent / t-BuOOH, V2O5 4: n-BuLi / tetrahydrofuran / 1 h / -78 °C 5: PdCl2, CuCl, O2 / dimethylformamide; H2O / 12 h / Ambient temperature 6: 1.) DBU, CH2Cl2, reflux, 1 hr 2.) Pd/C, H2, EtOH View Scheme |
4-Methylene-6-phenylsulfanyl-hexanal
isophytol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 62 percent / tetrahydrofuran / 2 h / Heating 2: 79 percent / t-BuOOH, V2O5 3: n-BuLi / tetrahydrofuran / 1 h / -78 °C 4: PdCl2, CuCl, O2 / dimethylformamide; H2O / 12 h / Ambient temperature 5: 1.) DBU, CH2Cl2, reflux, 1 hr 2.) Pd/C, H2, EtOH View Scheme |
Conditions | Yield |
---|---|
In octane | 100% |
Conditions | Yield |
---|---|
With hydroxylated magnesium fluoride In 1,2-propylene cyclic carbonate; n-heptane at 100℃; for 3h; | 99.9% |
With nanoscopic partly hydroxylated AlF3-50 In n-heptane; propylene carbonate at 100℃; for 1h; Friedel-Crafts alkylation; | 99.9% |
With 2,6-di-tert-butyl-pyridine; trimethylsilyl pentafluorophenylbis(trifluoromethanesulfonyl)methide In n-heptane Heating; | 97% |
Conditions | Yield |
---|---|
With hydrogenchloride; Zinc chloride In tetrachloromethane | 99.1% |
With hydrogenchloride; sodium dithionite; Zinc chloride In toluene | 99.8% |
With hydrogenchloride; zinc dibromide; zinc | 98.6% |
2-methylpropyl acetate
isophytol
Trimethylhydroquinone
Tocopherol
Conditions | Yield |
---|---|
With hydrogenchloride; Zinc chloride In water; toluene | 99.6% |
With hydrogenchloride; Zinc chloride In water; toluene | 98.6% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium chloride; Zinc chloride In water; toluene | 99.2% |
With hydrogen bromide; zinc dibromide In water | 99.1% |
With hydrogenchloride; Zinc chloride In water; toluene | 98.9% |
isophytol
(7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl bromide
Conditions | Yield |
---|---|
With pyridine; phosphorus tribromide In hexane at -10 - -7℃; for 3h; | 99% |
Conditions | Yield |
---|---|
With sodium hydroxide; sodium chloride; scandium tris(trifluoromethanesulfonate) In ethyl acetate; toluene | 99% |
Conditions | Yield |
---|---|
With hydrogenchloride; Zinc chloride In hexane; water; toluene | 98.1% |
With hydrogenchloride; Zinc chloride In hexane; water; toluene | 98.1% |
With hydrogenchloride; Zinc chloride In hexane; water; toluene | 95.9% |
With hydrogenchloride; Zinc chloride In hexane; water; toluene | 95.9% |
Conditions | Yield |
---|---|
With sodium chloride In ethyl acetate; toluene | 98% |
Conditions | Yield |
---|---|
Stage #1: isophytol; 2,3,5-trimethyl-1,4-hydroquinone diacetate With C8H15N2(1+)*Br(1-)*ZnBr2 In Petroleum ether at 70℃; for 6h; Stage #2: With acetic anhydride at 120℃; for 3h; Reagent/catalyst; Temperature; | 98% |
isophytol
Trimethylhydroquinone
A
vitamin E
B
2-phytyl-3,5,6-trimethylhydroquinone
Conditions | Yield |
---|---|
indium (III) iodide In Ethylene carbonate; n-heptane at 140 - 145℃; for 2h; Product distribution / selectivity; Heating / reflux; | A 97.3% B 0.25% |
indium(III) chloride In pentan-3-one at 140 - 145℃; for 5h; Product distribution / selectivity; Heating / reflux; | A 95.1% B 0.37% |
indium(III) chloride In Ethylene carbonate; n-heptane at 140 - 145℃; for 2 - 5h; Product distribution / selectivity; Heating / reflux; | A 94.8% B 0% |
Conditions | Yield |
---|---|
With dichromic acid; acetic acid In acetone at 50℃; for 14h; Reagent/catalyst; Temperature; | 97% |
With sodium periodate; acetic acid In acetone at 80℃; for 8h; Reagent/catalyst; Temperature; | 95% |
Conditions | Yield |
---|---|
With hydrogenchloride; aluminum (III) chloride In water; ethyl acetate at 60℃; for 6h; Temperature; Reagent/catalyst; Time; | 94.94% |
With acetic anhydride; acetic acid at 70℃; for 3h; Reagent/catalyst; Temperature; |
isophytol
Trimethylhydroquinone
A
vitamin E
B
(all-rac)-3,4-dehydro-α-tocopherol
Conditions | Yield |
---|---|
indium(III) chloride In n-heptane at 147℃; under 2550.26 Torr; for 3.1h; Product distribution / selectivity; | A 93.7% B n/a |
isophytol
4-acetoxy-2,3,5-trimethylphenol
A
vitamin E
B
(E,Z)-(all-rac)-3-phytyl-2,5,6-trimethylhydroquinone-1-acetate
Conditions | Yield |
---|---|
hafnium tetrakis(trifluoromethanesulfonate) In Ethylene carbonate; n-heptane at 80 - 140℃; for 1.66667h; Product distribution / selectivity; Heating / reflux; | A 1.4% B 0.2% C 93.3% |
scandium tris(trifluoromethanesulfonate) In Ethylene carbonate; n-heptane at 80 - 140℃; for 1.08333 - 1.66667h; Product distribution / selectivity; Heating / reflux; | A 0.5% B 0% C 90.7% |
silver trifluoromethanesulfonate In Ethylene carbonate; n-heptane at 80 - 140℃; for 1.08333 - 1.66667h; Product distribution / selectivity; Heating / reflux; | A 0.3% B 0% C 87% |
Conditions | Yield |
---|---|
In hexane; toluene | 93% |
Conditions | Yield |
---|---|
With hydroxylated magnesium fluoride In 1,2-propylene cyclic carbonate; n-heptane at 100℃; for 1h; | A 92.6% B n/a |
Conditions | Yield |
---|---|
methanetrisulfonic acid In Ethylene carbonate; n-heptane; water at 50 - 140℃; for 1 - 1.66667h; | 92.4% |
methanetrisulfonic acid In 1,2-propylene cyclic carbonate; n-heptane; water at 50 - 140℃; for 1h; | 91.2% |
SnTf(51)-MCM-41 In hexane at 100℃; for 1h; |
Conditions | Yield |
---|---|
With Nafion NR 50 In various solvent(s) at 100 - 140℃; under 760 Torr; for 1h; | A 92.3% B n/a |
With Nafion NR 50 In various solvent(s) at 100 - 140℃; under 760 Torr; for 1h; Product distribution; var. strong solid acids as catalysts; var. solv.; | A 92.3% B n/a |
With manganese(II) sulfate; monmorillonite K In benzene for 1.16667h; Heating; Title compound not separated from byproducts; | A 89% B n/a |
With scandium tris(trifluoromethanesulfonate) In xylene for 3h; Product distribution; Heating; var. solvents and rare earth metal(III) triflate; | |
With europium(III) trifluoroacetate In xylene for 3h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
gallium(III) triflate In Ethylene carbonate; n-heptane at 80 - 140℃; for 1.08333h; Product distribution / selectivity; Heating / reflux; | A 2.1% B 92.2% |
bismuth(lll) trifluoromethanesulfonate In Ethylene carbonate; n-heptane at 120 - 145℃; Product distribution / selectivity; Heating / reflux; | A 6.9% B 78.5% |
Conditions | Yield |
---|---|
92% |
Conditions | Yield |
---|---|
In toluene | 91% |
88.7% |
Conditions | Yield |
---|---|
With hydrogenchloride; sulfuric acid; oxalic acid; acetic anhydride In tetralin; n-heptane | 89% |
Conditions | Yield |
---|---|
Stage #1: Trimethylhydroquinone With sulfuric acid; toluene-4-sulfonic acid In ethyl acetate at 10℃; for 0.5h; Stage #2: isophytol With magnesium sulfate In ethyl acetate at 25 - 55℃; for 7h; Stage #3: acetic anhydride Further stages; | 89% |
Conditions | Yield |
---|---|
Stage #1: isophytol With phosphorus tribromide In n-heptane at -10 - 0℃; for 1h; Stage #2: With sodium hydroxide In water at 50 - 60℃; for 2h; pH=6 - 7; | 89% |
Multi-step reaction with 3 steps 1: hydrogenchloride; tetramethlyammonium chloride / water / 10 - 20 °C / Large scale 2: tetramethlyammonium chloride / acetonitrile / 50 - 60 °C / Large scale 3: sodium hydroxide; water / 40 - 50 °C / Large scale View Scheme |
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