25892-95-9

Basic information

• Product Name: 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethanone
• Synonyms: 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethanone;4'-Benzyloxy-6'-hydroxy-2',3'-dimethoxyacetophenone;1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one
• CAS NO: 25892-95-9
• Molecular Formula: C₁₇H₁₈O₅
• Molecular Weight: 302.32182
• Mol File: 25892-95-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 86–87°C
• Boiling Point: 470.1±40.0 °C(Predicted)
• Appearance: /
• Density: 1.199±0.06 g/cm3(Predicted)
• Refractive Index: 1.57
• Storage Temp.: 2-8°C
• PKA: 9.92±0.28(Predicted)
• CAS DataBase Reference: 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethanone(25892-95-9)
• EPA Substance Registry System: 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethanone(25892-95-9)

Safety Data

• Hazardous Substances Data: 25892-95-9(Hazardous Substances Data)

Usage

Preparation

Obtained by partial methylation of 4-(benzyloxy)-3,6-di-hydroxy-2-methoxyacetophenone, with dimethyl sulfate in the presence of potassium carbonate in refluxing acetone, for 5 h (57%).

InChI:InChI=1/C17H18O5/c1-11(18)15-13(19)9-14(16(20-2)17(15)21-3)22-10-12-7-5-4-6-8-12/h4-9,19H,10H2,1-3H3

Synthetic route

1-(4-(benzyloxy)-3,6-dihydroxy-2-methoxyphenyl)ethan-1-one (25892-94-8) + dimethyl sulfate (77-78-1) → 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9)

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 5h;	85%
With potassium carbonate In acetone Heating;	59%
In acetone for 5h; Reflux;

2-hydroxy-4,6-dimethoxyacetophenone (90-24-4) → 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 60 percent / aluminium chloride / chlorobenzene / 1 h / Heating 2: 99 percent / K2CO3 / acetone / Heating 3: 29 percent / NaOH; K2S2O8; pyridine / H2O / 24 h / 20 °C 4: 59 percent / K2CO3 / acetone / Heating View Scheme

2,4,6-trihydroxyacetophenone (480-66-0) → 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 92 percent / K2CO3 / acetone / 3 h / 65 °C 2: 60 percent / aluminium chloride / chlorobenzene / 1 h / Heating 3: 99 percent / K2CO3 / acetone / Heating 4: 29 percent / NaOH; K2S2O8; pyridine / H2O / 24 h / 20 °C 5: 59 percent / K2CO3 / acetone / Heating View Scheme

4,6-dihydroxy-2-methoxyacetophenone (3602-54-8) → 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / K2CO3 / acetone / Heating 2: 29 percent / NaOH; K2S2O8; pyridine / H2O / 24 h / 20 °C 3: 59 percent / K2CO3 / acetone / Heating View Scheme

1-(4-(benzyloxy)-2-hydroxy-6-methoxyphenyl)ethan-1-one (39548-89-5) → 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 29 percent / NaOH; K2S2O8; pyridine / H2O / 24 h / 20 °C 2: 59 percent / K2CO3 / acetone / Heating View Scheme
Multi-step reaction with 2 steps 1: pyridine; dipotassium peroxodisulfate; tetraethylammonium hydroxide / water / 24 h / 20 °C 2: acetone / 5 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: pyridine; tetraethylammonium hydroxide / water / 20 °C 1.2: 24 h / 20 °C 1.3: 1 h / 95 °C 2.1: potassium carbonate / acetone / 5 h / 60 °C View Scheme

1-(4-(benzyloxy)-3,6-dihydroxy-2-methoxyphenyl)ethan-1-one (25892-94-8) → 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9)

Conditions	Yield
In acetone

benzyl bromide (100-39-0) → 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 60 °C 3: potassium hydroxide; pyridine / diethylene glycol; water / 100 °C 4: pyridine; dipotassium peroxodisulfate; tetraethylammonium hydroxide / water / 24 h / 20 °C 5: acetone / 5 h / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetone / 5 h / 0 - 60 °C 2.1: potassium hydroxide / acetone / 5 h / 60 °C 3.1: sodium hydroxide; pyridine / water; diethylene glycol / 2 h / 100 °C 4.1: pyridine; tetraethylammonium hydroxide / water / 20 °C 4.2: 24 h / 20 °C 4.3: 1 h / 95 °C 5.1: potassium carbonate / acetone / 5 h / 60 °C View Scheme

5,7-dihydroxy-2-phenyl-chromen-4-one (480-40-0) → 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 60 °C 3: potassium hydroxide; pyridine / diethylene glycol; water / 100 °C 4: pyridine; dipotassium peroxodisulfate; tetraethylammonium hydroxide / water / 24 h / 20 °C 5: acetone / 5 h / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetone / 5 h / 0 - 60 °C 2.1: potassium hydroxide / acetone / 5 h / 60 °C 3.1: sodium hydroxide; pyridine / water; diethylene glycol / 2 h / 100 °C 4.1: pyridine; tetraethylammonium hydroxide / water / 20 °C 4.2: 24 h / 20 °C 4.3: 1 h / 95 °C 5.1: potassium carbonate / acetone / 5 h / 60 °C View Scheme

7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one (110506-85-9) → 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9)

Conditions	Yield
Multi-step reaction with 4 steps 2: potassium hydroxide; pyridine / diethylene glycol; water / 100 °C 3: pyridine; dipotassium peroxodisulfate; tetraethylammonium hydroxide / water / 24 h / 20 °C 4: acetone / 5 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: potassium hydroxide / acetone / 5 h / 60 °C 2.1: sodium hydroxide; pyridine / water; diethylene glycol / 2 h / 100 °C 3.1: pyridine; tetraethylammonium hydroxide / water / 20 °C 3.2: 24 h / 20 °C 3.3: 1 h / 95 °C 4.1: potassium carbonate / acetone / 5 h / 60 °C View Scheme

1-(4-(benzyloxy)-2-hydroxy-6-methoxyphenyl)ethanone (681294-57-5) → 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide; pyridine / diethylene glycol; water / 100 °C 2: pyridine; dipotassium peroxodisulfate; tetraethylammonium hydroxide / water / 24 h / 20 °C 3: acetone / 5 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; pyridine / water; diethylene glycol / 2 h / 100 °C 2.1: pyridine; tetraethylammonium hydroxide / water / 20 °C 2.2: 24 h / 20 °C 2.3: 1 h / 95 °C 3.1: potassium carbonate / acetone / 5 h / 60 °C View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 7-(benzyloxy)-5,6-dimethoxy-4H-chromen-4-one (34818-66-1)

Conditions	Yield
Stage #1: 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one; N,N-dimethyl-formamide dimethyl acetal In toluene at 80℃; for 18h; Stage #2: With hydrogenchloride In toluene at 0 - 50℃; for 1h;	97%
In toluene at 80℃; for 18h;	97%
Stage #1: 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one; N,N-dimethyl-formamide dimethyl acetal In 1,2-dimethoxyethane at 80℃; for 20h; Stage #2: With hydrogenchloride In water at 0 - 50℃; for 1h;	95%

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) + 4-benzyloxy-(14)COCl-benzoyl chloride → C30(14)CH28O7

Conditions	Yield
With pyridine at 20℃; for 3h;	81%

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 4-benzyloxy-2-hydroxy-3',4',5,6-tetra methoxy chalcone

Conditions	Yield
With potassium hydroxide In ethanol; water	75%

isovanillin (621-59-0) + 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → (E)-1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)-3-(3'-hydroxy-4'-methoxyphenyl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 48h;	53%
With potassium hydroxide In ethanol at 20℃; for 48h; Aldol Condensation;	53%

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) + 4-benzyloxy-3,5-dimethoxybenzoic acid chloride (14588-61-5) → 2,3-dimethoxy-4-benzyloxy-6-(3,5-dimethoxy-4-benzyloxy)-benzyloxyacetophenone (76015-45-7)

Conditions	Yield
With potassium carbonate In acetone for 2h; Heating;	52%

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) + 3,4-dimethoxy-benzaldehyde (120-14-9) → (E)-1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃; for 24h;	39%

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) + 3,4-dibenzyloxybenzoyl chloride (1486-54-0) → 2-(3,4-Dibenzyloxy-benzoyloxy)-4-benzyloxy-5,6-dimethoxyacetophenone (54544-06-8)

Conditions	Yield
With pyridine for 3h; Heating;	800 mg

4-(benzyloxy)benzoic acid chloride (1486-50-6) + 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 4-benzyloxy-benzoic acid 2-acetyl-5-benzyloxy-3,4-dimethoxy-phenyl ester

Conditions	Yield
With pyridine at 20℃; for 3h;

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → hispidulin (1447-88-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / 3 h / 20 °C 2: KOH / pyridine / 4 h / 60 °C 3: sulfuric acid / acetic acid / 1.5 h / 60 °C 4: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 7-benzyloxy-2-(4-benzyloxy-phenyl)-5,6-dimethoxy-chromen-4-one

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / 3 h / 20 °C 2: KOH / pyridine / 4 h / 60 °C 3: sulfuric acid / acetic acid / 1.5 h / 60 °C View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 1-(4-benzyloxy-6-hydroxy-2,3-dimethoxy-phenyl)-3-(4-benzyloxy-phenyl)-propane-1,3-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 3 h / 20 °C 2: KOH / pyridine / 4 h / 60 °C View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 5,7,4′-trihydroxy-6,3′,5′-trimethoxyflavone (76015-42-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 52 percent / K2CO3 / acetone / 2 h / Heating 2: 1.) KOH, Py; 2.) HOAc-NaOAc / 1.) 60 deg C, 30 min; 2.) reflux, 2 h 3: 61 percent / HCl / acetic acid / 3 h / Heating View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → Acetic acid 7-acetoxy-2-(4-acetoxy-3,5-dimethoxy-phenyl)-6-methoxy-4-oxo-4H-chromen-5-yl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: 52 percent / K2CO3 / acetone / 2 h / Heating 2: 1.) KOH, Py; 2.) HOAc-NaOAc / 1.) 60 deg C, 30 min; 2.) reflux, 2 h 3: 61 percent / HCl / acetic acid / 3 h / Heating 4: 22 mg / Py / 24 h / Ambient temperature View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 7,4'-dibenzyloxy-5,6,3',5'-tetramethoxyflavone

Conditions	Yield
Multi-step reaction with 2 steps 1: 52 percent / K2CO3 / acetone / 2 h / Heating 2: 1.) KOH, Py; 2.) HOAc-NaOAc / 1.) 60 deg C, 30 min; 2.) reflux, 2 h View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 2-Hydroxy-3',4',4-tribenzyloxy-5,6-dimethoxydibenzoylmethane (54544-07-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 800 mg / pyridine / 3 h / Heating 2: 450 mg / potassium hydroxide / pyridine / 2 h View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 3',4',7-trihydroxy-5,6-dimethoxyflavone (88153-47-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 800 mg / pyridine / 3 h / Heating 2: 450 mg / potassium hydroxide / pyridine / 2 h 3: 150 mg / sodium acetate, glacial acetic acid / 3 h / Heating 4: 40 mg / hydrogene / Pd/C (10percent) / ethyl acetate / 5 h View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 7,3',4'-Tribenzyloxy-5,6-dimethoxyflavone (54544-08-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 800 mg / pyridine / 3 h / Heating 2: 450 mg / potassium hydroxide / pyridine / 2 h 3: 150 mg / sodium acetate, glacial acetic acid / 3 h / Heating View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 1-(4,6-dihydroxy-2,3-dimethoxyphenyl)-3-(3'-hydroxy-4'-methoxyphenyl)propan-1-one

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / 48 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / 48 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 3-(3'-(benzyloxy)-4'-methoxyphenyl)-1-(4-(benzyloxy)-6-hydroxy-2,3 dimethoxyphenyl)propan-1-one

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide / ethanol / 48 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h 3: potassium carbonate / acetone / 3 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: potassium hydroxide / ethanol / 48 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h 3: potassium carbonate / acetone / 3 h / Reflux View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 7-(benzyloxy)-3-(3'-(benzyloxy)-4'-methoxybenzyl)-5,6-dimethoxy-4H-chromen-4-one

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium hydroxide / ethanol / 48 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h 3: potassium carbonate / acetone / 3 h / Reflux 4: toluene / 6 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: potassium hydroxide / ethanol / 48 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h 3: potassium carbonate / acetone / 3 h / Reflux 4: toluene / 6 h / Reflux View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 7-hydroxy-3-(3'-hydroxy-4'-methoxybenzyl)-5,6-dimethoxychroman-4-one

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium hydroxide / ethanol / 48 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h 3: potassium carbonate / acetone / 3 h / Reflux 4: toluene / 6 h / Reflux 5: palladium 10% on activated carbon; hydrogen / methanol / 1 h View Scheme
Multi-step reaction with 5 steps 1: potassium hydroxide / ethanol / 48 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h 3: potassium carbonate / acetone / 3 h / Reflux 4: toluene / 6 h / Reflux 5: palladium 10% on activated carbon; hydrogen / methanol / 1 h View Scheme
Multi-step reaction with 4 steps 1.1: toluene / 18 h / 80 °C 1.2: 1 h / 0 - 50 °C 2.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -60 °C 3.1: toluene-4-sulfonic acid / benzene / 12 h / 0 °C / Reflux; Acidic conditions 4.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: toluene / 18 h / 80 °C 1.2: 1 h / 0 - 50 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 0.08 h / -60 °C / Inert atmosphere 3.1: toluene-4-sulfonic acid / benzene / 12 h / 0 °C / Reflux; Acidic conditions 4.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: 1,2-dimethoxyethane / 20 h / 80 °C 1.2: 1 h / 0 - 50 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -60 °C 3.1: toluene-4-sulfonic acid / toluene / 12 h / 0 °C / Reflux 4.1: palladium 10% on activated carbon; hydrogen / methanol / 17 h / 20 °C View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 5,7-dihydroxy-6-methoxy-3-(3'-hydroxy-4'-methoxybenzyl)-4-chromanone (142546-12-1, 107585-69-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: potassium hydroxide / ethanol / 48 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h 3: potassium carbonate / acetone / 3 h / Reflux 4: toluene / 6 h / Reflux 5: palladium 10% on activated carbon; hydrogen / methanol / 1 h 6: 1-(Trimethylsilyl)imidazole / chloroform / 4 h / 0 - 60 °C View Scheme
Multi-step reaction with 6 steps 1: potassium hydroxide / ethanol / 48 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h 3: potassium carbonate / acetone / 3 h / Reflux 4: toluene / 6 h / Reflux 5: palladium 10% on activated carbon; hydrogen / methanol / 1 h 6: trimethylsilyl iodide / chloroform / 0.5 h / 0 - 60 °C View Scheme
Multi-step reaction with 5 steps 1.1: toluene / 18 h / 80 °C 1.2: 1 h / 0 - 50 °C 2.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -60 °C 3.1: toluene-4-sulfonic acid / benzene / 12 h / 0 °C / Reflux; Acidic conditions 4.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C 5.1: trimethylsilyl iodide / dichloromethane / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: toluene / 18 h / 80 °C 1.2: 1 h / 0 - 50 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 0.08 h / -60 °C / Inert atmosphere 3.1: toluene-4-sulfonic acid / benzene / 12 h / 0 °C / Reflux; Acidic conditions 4.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C 5.1: trimethylsilyl iodide / dichloromethane / 20 °C View Scheme

1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one (25892-95-9) → 7-(benzyloxy)-5,6-dimethoxychroman-4-one

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene / 18 h / 80 °C 1.2: 1 h / 0 - 50 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 0.08 h / -60 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: 1,2-dimethoxyethane / 20 h / 80 °C 1.2: 1 h / 0 - 50 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -60 °C View Scheme

Upstream product

• 681294-57-5 1-(4-(benzyloxy)-2-hydroxy-6-methoxyphenyl)ethanone 
• 110506-85-9 7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 100-39-0 benzyl bromide 
• 25892-94-8 1-(4-(benzyloxy)-3,6-dihydroxy-2-methoxyphenyl)ethan-1-one 
• 39548-89-5 1-(4-(benzyloxy)-2-hydroxy-6-methoxyphenyl)ethan-1-one 
• 3602-54-8 4,6-dihydroxy-2-methoxyacetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 54544-06-8 2-(3,4-Dibenzyloxy-benzoyloxy)-4-benzyloxy-5,6-dimethoxyacetophenone 
• 1447-88-7 hispidulin 
• 40983-99-1 2-(3,4-dimethoxyphenyl)-7-hydroxy-5,6-dimethoxy-4H-chromen-4-one 
• 22368-21-4 eupatilin 
• 52378-71-9 7-(benzyloxy)-2-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one 
• 34818-66-1 7-(benzyloxy)-5,6-dimethoxy-4H-chromen-4-one 
• 107585-74-0 5,7-dihydroxy-6-methoxy-3-(4'-hydroxybenzyl)-4-chromanone 

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