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inquiry3-chloro-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20 - 65℃; for 1.5h; Reagent/catalyst; Temperature; Solvent; Industrial scale; | 100% |
β-hydroxy-α-(2-methoxyphenoxy)4-hydroxy-3-methoxypropiophenone
A
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
B
2-methoxy-phenol
Conditions | Yield |
---|---|
With formic acid; N-ethyl-N,N-diisopropylamine; Lumogen F Orange 240 In acetonitrile at 25℃; for 8h; Reagent/catalyst; UV-irradiation; Inert atmosphere; | A 99% B 96% |
With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; | A 69% B 74% |
guaiacylglycerol-β-guaiacyl ether
A
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
B
2-methoxy-phenol
C
1-(3-methoxy-4-hydroxyphenyl)ethanone
Conditions | Yield |
---|---|
With oxygen; rose bengal In acetonitrile at 13℃; Irradiation; | A 28 % Chromat. B 15 % Chromat. C 30 % Chromat. |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
With water; barium carbonate |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
With sodium hydroxide |
4-benzyloxy-3-methoxyacetophenone
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 69 percent / Br2 / CHCl3; CCl4 / 1) 5 deg C, 20 min, 2) 5 deg C -> 40 deg C, 2 h 2: 95 percent / K2CO3 / dimethylformamide / 2 h / 25 °C 3: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 4: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 5: 28 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation View Scheme |
β-hydroxy-α-(2-methoxyphenoxy)4-hydroxy-3-methoxypropiophenone
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 2: 28 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation View Scheme |
3-methoxy-4-benzyloxy-α-bromoacetophenone
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95 percent / K2CO3 / dimethylformamide / 2 h / 25 °C 2: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 3: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 4: 28 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation View Scheme |
1-(4-(benzyloxy)-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 2: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 3: 28 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation View Scheme |
guaiacylglycerol-β-guaiacyl ether
A
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
B
2-methoxy-phenol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: oxygen; N-hydroxyphthalimide / acetone / 30 h / 20 °C / 760.05 Torr / Irradiation 2: N-ethyl-N,N-diisopropylamine; formic acid / acetonitrile / 24 h / 20 °C / Inert atmosphere; Irradiation View Scheme |
pinoresinol
A
3,4-Dihydroxybenzoic acid
B
3-methoxy-4-hydroxybenzoic acid
C
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
With potassium superoxide; sphingobacterium sp. T2 manganese superoxide dismutase In dimethyl sulfoxide for 1h; pH=7.8; Inert atmosphere; Enzymatic reaction; |
guaiacylglycerol-β-guaiacyl ether
A
coniferol
B
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
C
1-(4-hydroxy-3-methoxyphenyl)-2-propene-1-one
D
2-methoxy-phenol
Conditions | Yield |
---|---|
With 4ZnS*In2S3 In water; acetonitrile for 20h; Inert atmosphere; UV-irradiation; |
1-(4-hydroxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol
A
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
B
1-(4-hydroxy-3-methoxyphenyl)-2-propene-1-one
C
2-methoxy-phenol
Conditions | Yield |
---|---|
With 4ZnS*In2S3 In water; acetonitrile for 16h; Inert atmosphere; UV-irradiation; |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
3-chloro-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
With hydrogenchloride at 90℃; for 0.5h; | 96% |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; sodium hydroxide In water at 26℃; for 24h; | 79% |
With lithium aluminium tetrahydride In diethyl ether |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
acetic anhydride
ω-hydroxypropioguaiacone diacetate
Conditions | Yield |
---|---|
In pyridine for 24h; Ambient temperature; | 2 mg |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; sodium hydroxide / water / 24 h / 26 °C 2: methanesulfonic acid / water / 22.5 h / 65 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; sodium hydroxide / water / 24 h / 26 °C 2: triethylamine / isopropyl alcohol / 48 h / 85 - 90 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine / toluene / 16 h / -78 °C / Inert atmosphere; Resolution of racemate View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine / toluene / 16 h / -78 °C / Inert atmosphere; Resolution of racemate View Scheme |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere View Scheme |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 7.1: sodium acetate; hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C View Scheme |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 7.1: sodium acetate; hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C 8.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere View Scheme |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 7.1: sodium acetate; hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C 8.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere 9.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere View Scheme |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 7.1: sodium acetate; hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C 8.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere 9.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere 10.1: thionyl chloride / dichloromethane / 0.75 h / 20 °C / Inert atmosphere 10.2: 1.5 h / Inert atmosphere 11.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 12.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 2 h / -78 °C / Inert atmosphere 13.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 13.2: 1 h / Inert atmosphere 14.1: sodium azide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 15.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 1 h / 20 °C View Scheme |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere View Scheme |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone
1-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)prop-2-en-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere View Scheme |
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