480-47-7

Basic information

• Product Name: hydrangenol
• Synonyms: hydrangenol;3-(4-Hydroxyphenyl)-8-hydroxy-3,4-dihydro-1H-2-benzopyran-1-one;3-(4-Hydroxyphenyl)-8-hydroxyisochroman-1-one;3,4-Dihydro-8-hydroxy-3-(4-hydroxyphenyl)-1H-2-benzopyran-1-one;Hydrangel
• CAS NO: 480-47-7
• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.25
• EINECS: 200-258-5
• Mol File: 480-47-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 528.3 °C at 760 mmHg
• Flash Point: 206.4 °C
• Appearance: /
• Density: 1.386 g/cm³
• Vapor Pressure: 8.86E-12mmHg at 25°C
• Refractive Index: 1.661
• Storage Temp.: 2-8°C
• CAS DataBase Reference: hydrangenol(CAS DataBase Reference)
• NIST Chemistry Reference: hydrangenol(480-47-7)
• EPA Substance Registry System: hydrangenol(480-47-7)

Safety Data

• Hazardous Substances Data: 480-47-7(Hazardous Substances Data)

Usage

Description

Hydrangenol is the allergen of so me hydrangeaceae (Hortensia)

Definition

ChEBI: A member of the class of dihydroisocoumarins that is 3,4-dihydroisocoumarin substituted by a hydroxy group at position 8 and a 4-hydroxyphenyl group at position 3. It has been isolated from the roots of Scorzonera judaica and exhibits anti-all rgic activity.

Contact allergens

Hydrangenol is the allergen of hydrangea (Hydrangea macrophylla Thunb, Hydrangeaceae family).

InChI:InChI=1/C15H12O4/c16-11-6-4-9(5-7-11)13-8-10-2-1-3-12(17)14(10)15(18)19-13/h1-7,13,16-17H,8H2

Synthetic route

(+/-)-3-(4-methoxyphenyl)-8-methoxy-3,4-dihydroisocoumarin (82780-51-6) → hydrangenol (480-47-7)

Conditions	Yield
With boron tribromide In dichloromethane at -78 - 25℃;	94%
With boron tribromide In dichloromethane 1.) -78 deg C , 1 h , 2.) -78 deg C to RT , 12 h;	94%
With boron tribromide In dichloromethane at -78 - 20℃;	88%

3-(4'-benzyloxyphenyl)-8-hydroxy-3,4-dihydro-2-benzopyran-1-one (637774-32-4) → hydrangenol (480-47-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate under 3750.3 Torr;	84%

6-<2-(4-benzyloxyphenyl)ethenyl>salicylic acid → hydrangenol (480-47-7)

Conditions	Yield
With hydrogenchloride In methanol for 4h; Heating;	81%

Hydrangeaic acid (491-79-2, 113428-99-2) → hydrangenol (480-47-7) + (+/-)-hydromacrophyllol B + (+/-)-hydromacrophyllol A

Conditions	Yield
With copper dichloride In acetone for 3h; Heating;	A 75% B 11.2% C 5.1%

Hydrangenol-8-O-glucoside (67600-94-6) → hydrangenol (480-47-7)

Conditions	Yield
With sulfuric acid at 80 - 90℃; for 1h;	73.5%

methyl 2-(tert-butyldimethylsilyloxy)-6-(bromomethyl)-benzoate (1093748-41-4) + p-[(tert-butyldimethylsilyl)oxy]benzaldehyde (120743-99-9) → hydrangenol (480-47-7)

Conditions	Yield
Stage #1: methyl 2-(tert-butyldimethylsilyloxy)-6-(bromomethyl)-benzoate; p-[(tert-butyldimethylsilyl)oxy]benzaldehyde With titanocene(III) chloride In tetrahydrofuran at 20℃; for 17h; Stage #2: With sulfuric acid; water In tetrahydrofuran	51%

Hydrangeaic acid (491-79-2, 113428-99-2) → hydrangenol (480-47-7)

Conditions	Yield
at 180℃;

(Ξ)-8-β-D-glucopyranosyloxy-3-<4-hydroxy-phenyl>-isochroman-1-one → hydrangenol (480-47-7)

Conditions	Yield
With sulfuric acid

1-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-[2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-ethanol → hydrangenol (480-47-7)

Conditions	Yield
Stage #1: 1-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-[2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-ethanol With Trimethyl borate; sec.-butyllithium In tetrahydrofuran; hexane; cyclohexane at -78 - 20℃; Stage #2: With dihydrogen peroxide In acetic acid at 20℃; Stage #3: With trifluoroacetic acid In tetrahydrofuran; water Heating; Further stages.;

methyl 2-methyl-6-methoxybenzoate (79383-44-1) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / NBS; AIBN / CCl4 2: 53 percent / Cp2TiCl2 / tetrahydrofuran / 20 °C 3: 88 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

methyl 2-(bromomethoxy)-6-methoxybenzoate (943595-13-9) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 53 percent / Cp2TiCl2 / tetrahydrofuran / 20 °C 2: 88 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

p-[(tert-butyldimethylsilyl)oxy]benzaldehyde (120743-99-9) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sBuLi / tetrahydrofuran; cyclohexane; hexane / -78 °C 2.1: sBuLi; B(OMe)3 / tetrahydrofuran; cyclohexane; hexane / -78 - 20 °C 2.2: H2O2 / acetic acid / 20 °C 2.3: TFA / tetrahydrofuran; H2O / Heating View Scheme

4,5-dihydro-4,4-dimethyl-2-(2-methylphenyl)-2-oxazoline (71885-44-4) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sBuLi / tetrahydrofuran; cyclohexane; hexane / -78 °C 2.1: sBuLi; B(OMe)3 / tetrahydrofuran; cyclohexane; hexane / -78 - 20 °C 2.2: H2O2 / acetic acid / 20 °C 2.3: TFA / tetrahydrofuran; H2O / Heating View Scheme

p-benzyloxybenzaldehyde (4397-53-9) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 89 percent / sodium ethoxide / ethanol / 24 h / Heating 2: 94 percent / KOH / ethanol / 24 h / Heating 3: 87 percent / trifluoroacetic acid / 1,2-dichloro-ethane; H2O / 5 h / Heating 4: 84 percent / H2 / Pd/C / ethyl acetate / 3750.3 Torr View Scheme
Multi-step reaction with 5 steps 1: 68.2 percent / 10percent aq. NaOH / 14 h / Ambient temperature 2: 78 percent / dimethylformamide / 4 h / 80 °C 3: 1.) NaH, 2.) BuLi, 3.) Bf3*OEt2, 4.) KF 4: 90 percent / 10percent KOH / ethanol / 3 h / Heating 5: 81 percent / conc. HCl / methanol / 4 h / Heating View Scheme

(3-acetyloxy-2-ethoxycarbonylbenzyl)-triphenylphosphonium bromide (118842-88-9) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 89 percent / sodium ethoxide / ethanol / 24 h / Heating 2: 94 percent / KOH / ethanol / 24 h / Heating 3: 87 percent / trifluoroacetic acid / 1,2-dichloro-ethane; H2O / 5 h / Heating 4: 84 percent / H2 / Pd/C / ethyl acetate / 3750.3 Torr View Scheme

2-(4'-benzyloxyphenyl)-1-(3-hydroxy-2-ethoxycarbonylphenyl)ethene (148324-47-4) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / trifluoroacetic acid / 1,2-dichloro-ethane; H2O / 5 h / Heating 2: 84 percent / H2 / Pd/C / ethyl acetate / 3750.3 Torr View Scheme

2-(4'-benzyloxyphenyl)-1-(3-hydroxy-2-ethoxycarbonylphenyl)ethene (148324-45-2) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / KOH / ethanol / 24 h / Heating 2: 87 percent / trifluoroacetic acid / 1,2-dichloro-ethane; H2O / 5 h / Heating 3: 84 percent / H2 / Pd/C / ethyl acetate / 3750.3 Torr View Scheme

3-(4-methoxyphenyl)-7-methoxy-2-benzopyran-1(1H)-one (36640-12-7) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 2: 78 percent / BBr3 View Scheme

m-methoxyphenylacetic acid (1798-09-0) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 78.5 percent / polyphosphoric acid / 1.5 h / 70 - 75 °C 2: 1.) trimethyl orthoformate, methanol, p-toluenesulphonic acid, 2.) p-toluenesulphonic acid / 1.) heating, 15 min, 2.) benzene, heating 3: 1.) 1.6M butyllithium / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 4: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 5: 78 percent / BBr3 View Scheme
Multi-step reaction with 5 steps 1: 78.5 percent / polyphosphoric acid / 1.5 h / 70 - 75 °C 2: 1.) trimethyl orthoformate, methanol, p-toluenesulphonic acid, 2.) p-toluenesulphonic acid / 1.) heating, 15 min, 2.) benzene, heating 3: 1.) 1.6M butyllithium, 2.) CO2 / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 4: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 5: 78 percent / BBr3 View Scheme
Multi-step reaction with 6 steps 1: 78.5 percent / polyphosphoric acid / 1.5 h / 70 - 75 °C 2: 1.) trimethyl orthoformate, methanol, p-toluenesulphonic acid, 2.) p-toluenesulphonic acid / 1.) heating, 15 min, 2.) benzene, heating 3: 1.) 1.6M butyllithium, 2.) CO2 / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 4: 90 percent / 95percent phosphoric acid / 0.25 h / Heating 5: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 6: 78 percent / BBr3 View Scheme
Multi-step reaction with 5 steps 1: 78.5 percent / polyphosphoric acid / 1.5 h / 70 - 75 °C 2: 1.) trimethyl orthoformate, methanol, p-toluenesulphonic acid, 2.) p-toluenesulphonic acid / 1.) heating, 15 min, 2.) benzene, heating 3: 1.) 1.6M butyllithium, 2.) CO2 / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 4: 64 percent / sodium borohydride, 10percent NaOH 5: 78 percent / BBr3 View Scheme

methoxybenzene (100-66-3) + 2-chloro-decalin → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 78.5 percent / polyphosphoric acid / 1.5 h / 70 - 75 °C 2: 1.) trimethyl orthoformate, methanol, p-toluenesulphonic acid, 2.) p-toluenesulphonic acid / 1.) heating, 15 min, 2.) benzene, heating 3: 1.) 1.6M butyllithium / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 4: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 5: 78 percent / BBr3 View Scheme
Multi-step reaction with 5 steps 1: 78.5 percent / polyphosphoric acid / 1.5 h / 70 - 75 °C 2: 1.) trimethyl orthoformate, methanol, p-toluenesulphonic acid, 2.) p-toluenesulphonic acid / 1.) heating, 15 min, 2.) benzene, heating 3: 1.) 1.6M butyllithium, 2.) CO2 / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 4: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 5: 78 percent / BBr3 View Scheme
Multi-step reaction with 6 steps 1: 78.5 percent / polyphosphoric acid / 1.5 h / 70 - 75 °C 2: 1.) trimethyl orthoformate, methanol, p-toluenesulphonic acid, 2.) p-toluenesulphonic acid / 1.) heating, 15 min, 2.) benzene, heating 3: 1.) 1.6M butyllithium, 2.) CO2 / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 4: 90 percent / 95percent phosphoric acid / 0.25 h / Heating 5: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 6: 78 percent / BBr3 View Scheme
Multi-step reaction with 5 steps 1: 78.5 percent / polyphosphoric acid / 1.5 h / 70 - 75 °C 2: 1.) trimethyl orthoformate, methanol, p-toluenesulphonic acid, 2.) p-toluenesulphonic acid / 1.) heating, 15 min, 2.) benzene, heating 3: 1.) 1.6M butyllithium, 2.) CO2 / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 4: 64 percent / sodium borohydride, 10percent NaOH 5: 78 percent / BBr3 View Scheme

1′-(3-methoxyphenyl)-2′-(4′′-methoxyphenyl)ethan-2′-one (98540-26-2) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) trimethyl orthoformate, methanol, p-toluenesulphonic acid, 2.) p-toluenesulphonic acid / 1.) heating, 15 min, 2.) benzene, heating 2: 1.) 1.6M butyllithium / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 3: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 4: 78 percent / BBr3 View Scheme
Multi-step reaction with 4 steps 1: 1.) trimethyl orthoformate, methanol, p-toluenesulphonic acid, 2.) p-toluenesulphonic acid / 1.) heating, 15 min, 2.) benzene, heating 2: 1.) 1.6M butyllithium, 2.) CO2 / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 3: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 4: 78 percent / BBr3 View Scheme
Multi-step reaction with 5 steps 1: 1.) trimethyl orthoformate, methanol, p-toluenesulphonic acid, 2.) p-toluenesulphonic acid / 1.) heating, 15 min, 2.) benzene, heating 2: 1.) 1.6M butyllithium, 2.) CO2 / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 3: 90 percent / 95percent phosphoric acid / 0.25 h / Heating 4: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 5: 78 percent / BBr3 View Scheme
Multi-step reaction with 4 steps 1: 1.) trimethyl orthoformate, methanol, p-toluenesulphonic acid, 2.) p-toluenesulphonic acid / 1.) heating, 15 min, 2.) benzene, heating 2: 1.) 1.6M butyllithium, 2.) CO2 / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 3: 64 percent / sodium borohydride, 10percent NaOH 4: 78 percent / BBr3 View Scheme

3',4-dimethoxydeoxybenzoin ethylene acetal (117970-24-8) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) 1.6M butyllithium / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 2: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 3: 78 percent / BBr3 View Scheme
Multi-step reaction with 3 steps 1: 1.) 1.6M butyllithium, 2.) CO2 / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 2: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 3: 78 percent / BBr3 View Scheme
Multi-step reaction with 4 steps 1: 1.) 1.6M butyllithium, 2.) CO2 / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 2: 90 percent / 95percent phosphoric acid / 0.25 h / Heating 3: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 4: 78 percent / BBr3 View Scheme
Multi-step reaction with 3 steps 1: 1.) 1.6M butyllithium, 2.) CO2 / 1.) toluene, hexane, 24 h, 0 deg C, 2.) toluene, hexane, -20 deg C up to r.t. 2: 64 percent / sodium borohydride, 10percent NaOH 3: 78 percent / BBr3 View Scheme

3',4-dimethoxydeoxybenzoin-2'-carboxylic acid (117970-26-0) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / 95percent phosphoric acid / 0.25 h / Heating 2: 60 percent / H2 / 10percent Pt/C / tetrahydrofuran 3: 78 percent / BBr3 View Scheme
Multi-step reaction with 2 steps 1: 64 percent / sodium borohydride, 10percent NaOH 2: 78 percent / BBr3 View Scheme

5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-ol (66947-61-3) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran / Ambient temperature 2: 77 percent / PCC / CH2Cl2 / 12 h / Ambient temperature 3: 83 percent / BBr3 / CH2Cl2 / 3 h / Ambient temperature View Scheme

4-methoxy-benzaldehyde (123-11-5) + homopyrocatechol(?) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran / Ambient temperature 2: 77 percent / PCC / CH2Cl2 / 12 h / Ambient temperature 3: 83 percent / BBr3 / CH2Cl2 / 3 h / Ambient temperature View Scheme

3-(4'-Methoxyphenyl)-1-hydroxy-8-methoxyisochroman (157251-01-9) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / PCC / CH2Cl2 / 12 h / Ambient temperature 2: 83 percent / BBr3 / CH2Cl2 / 3 h / Ambient temperature View Scheme

1-(4-benzyloxyphenyl)but-1-en-3-one (75676-91-4) → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 78 percent / dimethylformamide / 4 h / 80 °C 2: 1.) NaH, 2.) BuLi, 3.) Bf3*OEt2, 4.) KF 3: 90 percent / 10percent KOH / ethanol / 3 h / Heating 4: 81 percent / conc. HCl / methanol / 4 h / Heating View Scheme

1-(4-benzyloxyphenyl)-5-dimethylamino-1,4-pentadien-3-one → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) NaH, 2.) BuLi, 3.) Bf3*OEt2, 4.) KF 2: 90 percent / 10percent KOH / ethanol / 3 h / Heating 3: 81 percent / conc. HCl / methanol / 4 h / Heating View Scheme

ethyl 6-<2-(4-benzyloxyphenyl)ethenyl>salicylate → hydrangenol (480-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / 10percent KOH / ethanol / 3 h / Heating 2: 81 percent / conc. HCl / methanol / 4 h / Heating View Scheme

hydrangenol (480-47-7) → Hydrangeaic acid (491-79-2, 113428-99-2)

Conditions	Yield
With potassium hydroxide In methanol for 1.5h; Heating;	100%
With sodium hydrogencarbonate In methanol

hydrangenol (480-47-7) → lunularic acid (23255-59-6)

Conditions	Yield
With sodium tetrahydroborate; palladium dichloride In methanol for 1h; Ambient temperature;	99.6%

hydrangenol (480-47-7) → dl-3,4-dihydro-8-hydroxy-3-(p-hydroxyphenyl)isocarbostyryl (80394-91-8)

Conditions	Yield
With ammonia In ethanol at 100℃; for 17h; autoclave;	64%

hydrangenol (480-47-7) → 2-hydroxy-6-methylbenzoic acid (567-61-3) + 4-hydroxy-benzoic acid (99-96-7)

Conditions	Yield
Bei der Kalischmelze;

hydrangenol (480-47-7) + tert-butyldimethylsilyl chloride (18162-48-6) → 8-(tert-Butyl-dimethyl-silanyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-isochroman-1-one (183619-44-5)

Conditions	Yield
With 1H-imidazole
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 4h;	240 mg

hydrangenol (480-47-7) + sodium amalgam + aqueous-alcoholic natrium carbonate → lunularic acid (23255-59-6)

Conditions	Yield

ethanol (64-17-5) + hydrangenol (480-47-7) + sodium → lunularic acid (23255-59-6)

Conditions	Yield

hydrangenol (480-47-7) + alkaline solution → Hydrangeaic acid (491-79-2, 113428-99-2)

Conditions	Yield

hydrangenol (480-47-7) + aq. barium hydroxide solution → Hydrangeaic acid (491-79-2, 113428-99-2)

Conditions	Yield

hydrangenol (480-47-7) + natrium carbonate solution → Hydrangeaic acid (491-79-2, 113428-99-2)

Conditions	Yield

hydrangenol (480-47-7) → 3'-Deoxythunberginol A (80458-94-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 240 mg / imidazole / dimethylformamide / 4 h / 25 °C 2: 89.9 percent / DDQ / benzene / 5 h / Heating 3: 100 percent / n-Bu4NF / tetrahydrofuran / 0.08 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: imidazole 2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone 3: n-Bu4NF View Scheme

Upstream product

• 637774-32-4 3-(4'-benzyloxyphenyl)-8-hydroxy-3,4-dihydro-2-benzopyran-1-one 
• 100-66-3 methoxybenzene 
• 1093748-41-4 methyl 2-(tert-butyldimethylsilyloxy)-6-(bromomethyl)-benzoate 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 82780-49-2 2-[2-Hydroxy-2-(4-methoxy-phenyl)-ethyl]-6-methoxy-N,N-dimethyl-benzamide 
• 82780-48-1 N,N-Dimethyl-2-methoxy-6-methylbenzamide 
• 7291-34-1 2-methoxy-N,N-dimethylbenzamide 
• 75676-91-4 1-(4-benzyloxyphenyl)but-1-en-3-one 
• 157251-01-9 3-(4'-Methoxyphenyl)-1-hydroxy-8-methoxyisochroman 
• 66947-61-3 5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-ol 
• 117970-26-0 3',4-dimethoxydeoxybenzoin-2'-carboxylic acid 
• 117970-24-8 3',4-dimethoxydeoxybenzoin ethylene acetal 
• 98540-26-2 1′-(3-methoxyphenyl)-2′-(4′′-methoxyphenyl)ethan-2′-one 

Downstream Products

• 23255-59-6 lunularic acid 
• 491-79-2 Hydrangeaic acid 
• 157598-00-0 (+/-)-hydromacrophyllol A 
• 157598-00-0 (+/-)-hydromacrophyllol B 
• 183619-48-9 8-(tert-Butyl-dimethyl-silanyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-isochromen-1-one 
• 80458-94-2 3'-Deoxythunberginol A 
• 80394-91-8 dl-3,4-dihydro-8-hydroxy-3-(p-hydroxyphenyl)isocarbostyryl 
• 183619-44-5 8-(tert-Butyl-dimethyl-silanyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-isochroman-1-one 
• 567-61-3 2-hydroxy-6-methylbenzoic acid 
• 99-96-7 4-hydroxy-benzoic acid 

Relevant articles and documents

Titanocene(III) chloride mediated radical-induced synthesis of 3,4-dihydroisocoumarins: synthesis of (±)-hydrangenol, (±)-phyllodulcin, (±)-macrophyllol and (±)-thunberginol G

A radical-promoted synthesis of 3,4-dihydroisocoumarins has been achieved in moderate to good yields using titanocene(III) chloride (Cp2TiCl) as the radical initiator. The total synthesis of four naturally occurring dihydrocoumarins hydrangenol, phyllodulcin, macrophyllol and thunberginol G has been accomplished using the radical technology. Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and Zn-dust in THF under argon.

Synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins via successive lateral and ortho-lithiations of 4,4-dimethyl-2-(o-tolyl)oxazoline

Sequential treatment of 4,4-dimethyl-2-(o-tolyl)oxazoline in THF with sec-BuLi, aromatic or aliphatic aldehydes, sec-BuLi, B(OMe)3, and H2O2 produced the laterally alkylated and ortho-hydroxylated oxazolines in one-pot. Treatment of these products with TFA in aqueous THF provided 3-substituted 8-hydroxy-3,4-dihydroisocoumarins in 44-75% overall yields. This procedure allowed the short synthesis of (±)-hydrangenol and (±)-phyllodulcin, naturally occurring 3,4-dihydroisocoumarins of pharmacological interest. A more economical synthesis of (±)-phyllodulcin via the trianion intermediate is also described.

Development of bioactive functions in Hydrangeae Dulcis Folium. VI. Syntheses of thunberginols A and F and their 3'-deoxy-derivatives using regiospecific lactonization of stilbene carboxylic acid: Structures and inhibitory activity on histamine release of hydramacrophyllols A and B

Lactonization reaction of 2-carboxystilbene mediated by copper(II) chloride proceeded regiospecifically to give the five-membered lactone, while the bromolactonizations using N-bromosuccinimide and anodic oxidation were found to furnish the six-membered lactone. Using these regiospecific lactonization reactions as a key step, antiallergic and antimicrobial isocoumarins and the benzylidenephthalides thunberginols A and F and their 3'-deoxyanalogs were synthesized from phyllodulcin and hydrangenol. Two phthalides called hydramacrophyllols A and B were isolated from Hydrangeae Dulcis Folium and their stereostructures were determined on the basis of physicochemical and chemical evidence, which included the syntheses of hydramacrophyllols A and B from hydrangenol by the application of the lactonization method using copper(II) chloride. In addition, hydramacrophyllols A and B were found to exhibit an inhibitory effect on the histamine release from rat peritoneal exudate cells induced by antigen- antibody reaction.