533-31-3

Basic information

• Product Name: Sesamol
• Synonyms: 4-Hydroxy-1,2-Methylenedioxybenzene;NSC 59256;5-Hydroxy-1,3-benzodioxole 3,4-Methylenedioxyphenol;3,4-METHYLENEDIOXYPHENOL FOR SYNTHESIS;1,2,4-Benzenetriol Methylene ether;1,3-Benzodioxol-5-ol, 9CI;benzo[d][1,3]dioxol-5-ol;4-hydroxy-1,3-benzodioxole
• CAS NO: 533-31-3
• Molecular Formula: C₇H₆O₃
• Molecular Weight: 138.12
• EINECS: 208-561-5
• Product Categories: Phenols;Aromatic Phenols;Phenoles and thiophenoles;API intermediates;Building Blocks;C6 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 533-31-3.mol
• Article Data: 60

Chemical Properties

• Melting Point: 62-65 °C(lit.)
• Boiling Point: 113-116°C 2mm
• Flash Point: 113-116°C/2mm
• Appearance: off-white to tan/crystalline
• Density: 1.2112 (rough estimate)
• Refractive Index: 1.4850 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform, Methanol
• PKA: 10.08±0.20(Predicted)
• Water Solubility: slightly soluble
• Sensitive: Light Sensitive
• BRN: 127405
• CAS DataBase Reference: Sesamol(CAS DataBase Reference)
• NIST Chemistry Reference: Sesamol(533-31-3)
• EPA Substance Registry System: Sesamol(533-31-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: SM0890000
• TSCA: Yes
• Hazardous Substances Data: 533-31-3(Hazardous Substances Data)

Usage

Description

Sesamol is found in sesame seeds and sesame oil. It is a well-known antioxidant. It has antioxidant, chemoprevention, antimutagenic, and antihepatotoxic activities and can induce the apoptosis of cancer and cardiovascular cells. It can be used in the synthesis of paroxetine.

Reference

M. A. Ansari, Z. Fatima, S. Hameed, Sesamol: A Natural Phenolic Compound with Promising Anticandidal Potential, Journal of Pathogens, vol. 2014, Article ID 895193 T. Geetha, B. Rohit, K. Pal, Sesamol: an efficient antioxidant with potential therapeutic benefits, Medicinal Chemistry, 2009, vol. 5, pp. 367-371

Chemical Properties

off-white to beige crystalline powder

Uses

Different sources of media describe the Uses of 533-31-3 differently. You can refer to the following data:
1. Sesamol is a natural component of sesame oil with antioxidant activity. Sesamol has potential protective effects against free radicals as well as some antifungal activity. Sesamol can also be used as an intermediate in the preparation of antidepressants such as Paroxetine (P205750).
2. Sesamol (Paroxetine Anhydrous EP Impurity B) is a natural component of sesame oil with antioxidant activity. Sesamol has potential protective effects against free radicals as well as some antifungal activity. Sesamol can also be used as an intermediate in the preparation of antidepressants such as Paroxetine (P205750).

Synthesis Reference(s)

Tetrahedron Letters, 19, p. 3085, 1978 DOI: 10.1016/S0040-4039(01)94947-0

General Description

Sesamol, a principal phytophenol of sesame oil lignans, is typically used as a dietary compound.(10)

InChI:InChI=1/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2

Synthetic route

5-iodo-1,3-benzodioxole (5876-51-7) → Sesamol (533-31-3)

Conditions	Yield
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; potassium hydroxide In water; dimethyl sulfoxide at 60℃; for 24h; Schlenk technique; Inert atmosphere;	99%
With copper(I) oxide; 1D-1-O-Methyl-muco-inostol; sodium hydroxide In water at 130℃; for 6h;	59%
With formic acid; oxygen; triethylamine; copper(ll) bromide In acetonitrile at 20℃; for 48h; Irradiation;	52%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) → Sesamol (533-31-3)

Conditions	Yield
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 80℃; for 24h; Schlenk technique; Inert atmosphere;	99%
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 120℃; for 24h; Glovebox; Irradiation; Inert atmosphere;	72%
Stage #1: 1,2-(methylenedioxy)-4-bromobenzene With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: With oxaziridine In tetrahydrofuran at 0 - 25℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	63%

piperonal (120-57-0) → Sesamol (533-31-3)

Conditions	Yield
Stage #1: piperonal With 3-chloro-benzenecarboperoxoic acid for 0.0833333h; Dakin oxidation; Stage #2: With sodium hydroxide for 0.0833333h; Further stages.;	95%
With sulfuric acid; dihydrogen peroxide; boric acid In tetrahydrofuran; water at 20℃; for 3.5h; Oxidation;	89%
With sulfuric acid; dihydrogen peroxide; boric acid; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 0℃; Dakin reaction;	78%

benzo[d][1,3]dioxol-5-yl 4-methylbenzenesulfonate (16387-85-2) → Sesamol (533-31-3)

Conditions	Yield
With magnesium In methanol for 4h; Ambient temperature;	95%
With potassium fluoride on basic alumina for 0.05h; Substitution; microwave irradiation;	88%
With (2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)-diphenylphosphine; bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; carbon dioxide; tetrabutylammomium bromide; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 4h; Irradiation;	31%

acetic acid benzo[1,3]dioxol-5-yl ester (326-58-9) → Sesamol (533-31-3)

Conditions	Yield
With water; potassium hydroxide In methanol at 50℃; for 2h;	95%
With water at 20℃; for 1.25h;	95%

sodium 1,3-benzodioxol-5-olate → Sesamol (533-31-3)

Conditions	Yield
With hydrogenchloride In water pH=8.5;	94.3%

5-(2-Methoxy-ethoxymethoxy)-benzo[1,3]dioxole (87770-73-8) → Sesamol (533-31-3)

Conditions	Yield
With 2-chloro-1,3,2-dithioborolane In dichloromethane at -78℃; for 0.75h;	94%

5-propionyloxy-benzo[1,3]dioxole (112579-46-1) → Sesamol (533-31-3)

Conditions	Yield
Stage #1: 5-propionyloxy-benzo[1,3]dioxole With sodium hydroxide; tetrabutyl-ammonium chloride; water In dichloromethane at 20 - 25℃; for 8 - 8.75h; Stage #2: With hydrogenchloride In dichloromethane; water pH=8.5;	92.3%

3,4-(methylenedioxy)-benzeneboronic acid (94839-07-3) → Sesamol (533-31-3)

Conditions	Yield
With 2,5-dimethylfuran; zinc(II) phthalocyanine; oxygen In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h; Irradiation; Sealed tube; Schlenk technique;	92%
With dihydrogen peroxide In water at 20℃; for 0.0833333h;	92%
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 24h; Green chemistry;	88%
With rongalite In ethanol; water at 20℃; for 7h; Irradiation;	71%
With [Rh2(bpy)2(μ-OAc)2(OAc)2]; oxygen; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide under 760.051 Torr; for 18h; Irradiation;	30 mg

5-(4-methoxy-benzyloxy)-benzo[1,3]dioxole → Sesamol (533-31-3)

Conditions	Yield
With carbon tetrabromide In methanol for 5h; ether cleavage; Heating;	91%

5-chloro-1,3-benzodioxole (7228-38-8) → Sesamol (533-31-3)

Conditions	Yield
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; Inert atmosphere;	88%
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; caesium carbonate In water; N,N-dimethyl-formamide at 130℃; for 0.5h; Inert atmosphere; Microwave irradiation;	51%

C15H12O5 → Sesamol (533-31-3)

Conditions	Yield
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.25h; chemoselective reaction;	88%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → Sesamol (533-31-3)

Conditions	Yield
Stage #1: 1-(benzo[d][1,3]dioxol-6-yl)ethanone With formic acid In toluene at 30 - 40℃; for 0.5h; Stage #2: With dihydrogen peroxide In toluene for 12h; Stage #3: With water at 35 - 40℃; for 4h; Concentration; Alkaline conditions;	82.5%

3,4-methylenedioxyphenyl formate (80592-18-3) → Sesamol (533-31-3)

Conditions	Yield
With water; potassium hydroxide In methanol at 50℃; for 1h;	82%
With potassium hydroxide In tetrahydrofuran; methanol at 10℃; for 30h; Yield given;
With potassium hydroxide In methanol for 1h; Ambient temperature; Yield given;

3,4-methylenedioxy-1-(2-tetrahydropyranyloxy)benzene (28577-94-8) → Sesamol (533-31-3)

Conditions	Yield
With titanium(III) chloride In acetonitrile at 20℃; for 24h;	81%

3,4-methylenedioxyphenyl formate (80592-18-3) → Sesamol (533-31-3) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With ethanol; sodium hydroxide at 82 - 96℃; for 4.5h; Reflux; elimination of ethyl formate;	A 79% B n/a

4-methoxy-3,4-(methylenedioxy)cyclohexa-2,5-dienone (57197-23-6) + methyl 7-methoxy-2-methyl-4-oxo-4H-chromene-3-carboxylate → Sesamol (533-31-3) + 6-hydroxy-10,13b-dimethoxy-5H-[1,3]dioxolo[4',5':3,4]benzo[1,2-b]xanthene-5,7(13bH)-dione

Conditions	Yield
With lithium hexamethyldisilazane In toluene at 0℃; for 0.5h; Reflux; regioselective reaction;	A 46 mg B 72%

5-methoxybenzo[d]1,3-dioxole (7228-35-5) → Sesamol (533-31-3)

Conditions	Yield
With copper(I) oxide; sodium methylate In methanol at 185℃; for 12h; Autoclave;	68%

methanol (67-56-1) + piperonal (120-57-0) → Sesamol (533-31-3) + methyl 3,4-methylenedioxybenzoate (326-56-7)

Conditions	Yield
With dihydrogen peroxide; sulfuric acid In methanol for 24h; Ambient temperature;	A 67% B 8%

piperonal (120-57-0) → Sesamol (533-31-3) + methyl 3,4-methylenedioxybenzoate (326-56-7)

Conditions	Yield
With dihydrogen peroxide; sulfuric acid In methanol for 24h; Ambient temperature;	A 67% B 8%

(3,4-methylenedioxy)phenylmagnesium bromide (17680-04-5) → Sesamol (533-31-3)

Conditions	Yield
With air In tetrahydrofuran at -25℃; under 12929 Torr; for 0.0566667h; Green chemistry;	57%

8-methyl-6H-[1,3]dioxolo[4,5-g]chromen-6-one → Sesamol (533-31-3) + 2-isopropyl-4,5-(methylenedioxy)phenol (1415385-84-0)

Conditions	Yield
With potassium hydroxide In ethylene glycol Mechanism; Reflux;	A 53% B 17%

carbon dioxide (124-38-9) + C11H14O5S → Sesamol (533-31-3) + Piperonylic acid (94-53-1)

Conditions	Yield
With (2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)-diphenylphosphine; bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; tetrabutylammomium bromide; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 4h; Irradiation;	A 21% B 12%

3,4-methylenedioxypropiophenone (28281-49-4) → Sesamol (533-31-3)

Conditions	Yield
With formic acid; dihydrogen peroxide anschliessend Behandeln mit methanol. Kalilauge;
Stage #1: 3,4-methylenedioxypropiophenone With acetic anhydride; toluene-4-sulfonic acid In dichloromethane at 40℃; Stage #2: With dihydrogen peroxide In dichloromethane; water Heating / reflux; Stage #3: With hydrogenchloride In dichloromethane; water pH=1;
Stage #1: 3,4-methylenedioxypropiophenone In dichloromethane at 40℃; for 10h; Heating / reflux; Stage #2: With hydrogenchloride In dichloromethane; water pH=1; Heating / reflux;
Stage #1: 3,4-methylenedioxypropiophenone With phthalic anhydride; toluene-4-sulfonic acid In dichloromethane at 40℃; Stage #2: With dihydrogen peroxide In dichloromethane; water Heating / reflux; Stage #3: With hydrogenchloride In dichloromethane; water pH=1;
Stage #1: 3,4-methylenedioxypropiophenone With maleic anhydride; toluene-4-sulfonic acid In dichloromethane at 40℃; Stage #2: With dihydrogen peroxide In dichloromethane; water Heating / reflux; Stage #3: With hydrogenchloride In dichloromethane; water pH=1;

benzo[1,3]dioxolo-5-ylamine (14268-66-7) → Sesamol (533-31-3)

Conditions	Yield
Diazotization;

sesamolin → Sesamol (533-31-3)

Conditions	Yield
at 180℃; for 2h; Product distribution; variation of time, temperature; sesamol enhances antioxidativ action of γ-tocopherol;

piperonyl butoxide → Sesamol (533-31-3)

Conditions	Yield
With hydrogenchloride for 1h; Elimination;

sesamolin → Sesamol (533-31-3)

Conditions	Yield
With mineral acids
With hydrogenchloride

sesamol radical cation → Sesamol (533-31-3)

Conditions	Yield
With triethylamine In various solvent(s) at 20℃; Kinetics; Further Variations:; Reagents;

Sesamol (533-31-3) + dimethyl sulfate (77-78-1) → 5-methoxybenzo[d]1,3-dioxole (7228-35-5)

Conditions	Yield
With tetraethylammonium hydroxide at 0 - 20℃; for 1h;	100%
With sodium hydroxide In water for 1h; Heating;	99%
With potassium hydroxide
With potassium carbonate In acetone Heating; Yield given;
Alkaline conditions;

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + Sesamol (533-31-3) → 2,3-(methylenedioxy)benzo[b]naphtho[2,3-d]furan-7,11-dione

Conditions	Yield
With potassium hydroxide In pyridine at 90℃;	100%

Sesamol (533-31-3) + tert-butyldimethylsilyl chloride (18162-48-6) → (benzo[d][1,3]dioxol-5-yloxy)(tert-butyl)dimethylsilane (197522-91-1)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	98%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0 - 23℃; for 4h; Inert atmosphere;	96%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 14h; silylation;	92%
With 1H-imidazole In dichloromethane at 20℃; for 16h;

3-phenyl-propionaldehyde (104-53-0) + Sesamol (533-31-3) → C23H20O6

Conditions	Yield
Stage #1: Sesamol With ethylmagnesium bromide In diethyl ether at 20℃; for 0.333333h; Stage #2: 3-phenyl-propionaldehyde In dichloromethane for 20h; Heating;	100%

Sesamol (533-31-3) + ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate (24393-56-4) → 8-(4-methoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]-chromen-6-one (267901-33-7)

Conditions	Yield
With trifluoroacetic acid at 20℃; for 24h;	100%

Sesamol (533-31-3) + dimethylsulfide (75-18-3) → 5-methoxybenzo[d]1,3-dioxole (7228-35-5)

Conditions	Yield
Stage #1: Sesamol With tetraethylammonium hydroxide In methanol Stage #2: dimethylsulfide In tetrahydrofuran at 20℃; for 1h;	100%

Sesamol (533-31-3)

Conditions	Yield
Stage #1: Sesamol With isopropylmagnesium chloride In tetrahydrofuran at 0 - 4℃; for 2h; Industry scale; Stage #2: indole-2,3-dione In tetrahydrofuran at -5 - 3℃; Industry scale; Stage #3: With water; ammonium chloride In tetrahydrofuran at 3 - 4℃; Industry scale;	100%
Stage #1: Sesamol With isopropylmagnesium chloride In tetrahydrofuran at 0 - 5℃; for 2.5h; Stage #2: indole-2,3-dione In tetrahydrofuran at 0 - 20℃; for 19h;	98%
With potassium carbonate In tetrahydrofuran for 17h; Solvent; Inert atmosphere;
With triethylamine In tert-butyl methyl ether at 25℃; for 15h; Inert atmosphere;
In water at 20℃;

4-(4-fluorobenzenesulfonyl)-1-prop-2-ynylpiperidine-4-carboxylic acid ethyl ester (226396-64-1) + Sesamol (533-31-3) → C24H25NO7S (226396-68-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;	100%

Sesamol (533-31-3) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → C13H9NO7S

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.166667h;	100%

Sesamol (533-31-3) + ethanol (64-17-5) → 4-ethoxy-3,4-(methylenedioxy)cyclohexa-2,5-dienone (57197-24-7)

Conditions	Yield
With potassium carbonate; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile for 0.166667h; Ambient temperature;	99%

Sesamol (533-31-3) + chloromethyl methyl ether (107-30-2) → (3,4-methylenedioxyphenoxy)methyl methyl ether (111726-43-3)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1.) 0 deg C, 30 min, 2.) 0 deg C, 3 h;	99%
Stage #1: Sesamol With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: chloromethyl methyl ether In tetrahydrofuran at 20℃; for 24h;	98%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;	98%

Sesamol (533-31-3) + allyl bromide (106-95-6) → O-allyl-sesamol (19202-22-3)

Conditions	Yield
With potassium carbonate In acetone at 25℃; for 12h;	99%
With PS-BEMP; N,N-dimethyl-formamide In acetonitrile	98%
With PS-BEMP In N,N-dimethyl-formamide; acetonitrile at 20℃; for 3h;	98%

Sesamol (533-31-3) + t-butyldimethylsiyl triflate (69739-34-0) → (benzo[d][1,3]dioxol-5-yloxy)(tert-butyl)dimethylsilane (197522-91-1)

Conditions	Yield
With triethylamine In dichloromethane at -78℃; for 1h;	99%

Sesamol (533-31-3) + benzyl bromide (100-39-0) → 5-(benzyloxy)benzo[d][1,3]dioxole (66177-24-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 23℃; Inert atmosphere; Schlenk technique;	99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h;	95%
With potassium carbonate at 60℃; for 3h;
Stage #1: Sesamol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 12h;

Sesamol (533-31-3) + (E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) → 8-(4-methoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]-chromen-6-one (267901-33-7)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 24h;	99%
With trifluoroacetic acid; palladium diacetate In dichloromethane at 20℃; for 10h; Cyclization; hydroarylation;	96%

Sesamol (533-31-3) + 4-methoxy-benzaldehyde (123-11-5) → 2,2'-dihydroxy-4''-methoxy-4,5:4',5'-dimethylenedioxytriphenylmethane

Conditions	Yield
With boron trifluoride diethyl etherate In benzene at 20℃; for 1h;	99%
Stage #1: Sesamol With ethylmagnesium bromide In diethyl ether at 20℃; for 0.333333h; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde In dichloromethane for 19h; Inert atmosphere; Reflux;

Sesamol (533-31-3) + (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → tert-butyl (R)-4-((R)-hydroxy(6-hydroxybenzo[d][1,3]dioxol-5-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (925703-84-0)

Conditions	Yield
Stage #1: Sesamol With methylmagnesium chloride In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In dichloromethane at 0 - 20℃; for 15h;	99%

Sesamol (533-31-3) + C16H20O6 → C23H24O8 (1083302-78-6)

Conditions	Yield
With iron(III) chloride In dichloromethane at 20℃; for 0.333333h; Friedel Crafts alkylation; optical yield given as %de; diastereoselective reaction;	99%

Sesamol (533-31-3) + (4aS,8aS)-3,4,4aα,5,6,7,8,8aβ-octahydro-5,5,8aβ-trimethyl-1-methylidene-2(1H)-naphthalenone (59633-90-8) → (12bS)-9,10-methylenedioxy-4,4,12b-trimethyl-2,3,4,4a,5,6,12,12b-octahydro-1Hbenzo[a]xanthene (1150626-77-9)

Conditions	Yield
With Amberlyst A-15 ion exchange resin In benzene for 1.83333h; Friedel Crafts alkylation; Inert atmosphere; Reflux; Molecular sieve;	99%

Sesamol (533-31-3) + 2-(2-nitrovinyl)naphthalene (37629-37-1, 21461-46-1) → C19H15NO5 (1236039-26-1)

Conditions	Yield
With C36H45F12N7S2 In toluene at 20℃; for 12h; Friedel Crafts reaction; optical yield given as %ee; enantioselective reaction;	99%
With C36H45F12N7S2 In toluene at 20℃; for 12h; Friedel Crafts reaction; optical yield given as %ee; stereoselective reaction;	99%

Sesamol (533-31-3) + 1-chloro-4-(2-nitrovinyl)benzene (706-07-0) → C15H12ClNO5 (1236039-19-2)

Conditions	Yield
With C36H45F12N7S2 In toluene at 20℃; for 12h; Friedel Crafts reaction; optical yield given as %ee; enantioselective reaction;	99%
With C36H45F12N7S2 In toluene at 0℃; for 12h; Friedel Crafts reaction; optical yield given as %ee; stereoselective reaction;	91%

Sesamol (533-31-3) + tert-butylchlorodiphenylsilane (58479-61-1) → C23H24O3Si

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	99%

Sesamol (533-31-3) + 1-benzyloxyallene (67515-49-5) → (S)-5-(1-(benzyloxy)allyloxy)-2-chloro-1,3-dimethylbenzene

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; triethylamine In 1,4-dioxane at 15℃; for 12h; Schlenk technique; Molecular sieve; enantioselective reaction;	99%

Sesamol (533-31-3) + 2-phenyl-indole (948-65-2) + 2,2-dihydroxy-1-phenyl-ethanone (1075-06-5) → 2-phenyl-3-(6-phenyl-[1,3]dioxolo[4,5-f]benzofuran-7-yl)-1H-indole

Conditions	Yield
With toluene-4-sulfonic acid In nitromethane at 80℃; for 3h;	99%
With 3-(1,1-dioxido-4-(3-(3-(3-sulfopropyl)-1H-imidazol-3-ium-1-yl)propyl)thiomorpholino-4-ium)propane-1-sulfonate trifluoromethanesulfonate In acetic acid butyl ester at 80℃; for 2h;	99%

Sesamol (533-31-3) + ethyl (1-benzyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene)cyanoacetate (26960-51-0) → C27H22N2O6

Conditions	Yield
With C29H28F6N4OS at 25℃; Molecular sieve; enantioselective reaction;	99%

Sesamol (533-31-3) + C20H15FN2O3 → C27H21FN2O6

Conditions	Yield
With C29H28F6N4OS at 25℃; Molecular sieve; enantioselective reaction;	99%

Sesamol (533-31-3) + C20H15ClN2O3 → C27H21ClN2O6

Conditions	Yield
With C29H28F6N4OS at 25℃; Molecular sieve; enantioselective reaction;	99%

Sesamol (533-31-3) + C20H15BrN2O3 → C27H21BrN2O6

Conditions	Yield
With C29H28F6N4OS at 25℃; Molecular sieve; enantioselective reaction;	99%

Sesamol (533-31-3) + C21H18N2O3 → C28H24N2O6

Conditions	Yield
With C29H28F6N4OS at 25℃; Molecular sieve; enantioselective reaction;	99%

Sesamol (533-31-3) + C20H15ClN2O3 → C27H21ClN2O6

Conditions	Yield
With C29H28F6N4OS at 25℃; Molecular sieve; enantioselective reaction;	99%

Upstream product

• 120-57-0 piperonal 
• 28281-49-4 3,4-methylenedioxypropiophenone 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 80592-18-3 3,4-methylenedioxyphenyl formate 
• 67-56-1 methanol 
• 87770-73-8 5-(2-Methoxy-ethoxymethoxy)-benzo[1,3]dioxole 
• 64-18-6 formic acid 
• 274-09-9 Methylenedioxybenzene 
• 112579-46-1 5-propionyloxy-benzo[1,3]dioxole 
• 7228-38-8 5-chloro-1,3-benzodioxole 
• 5876-51-7 5-iodo-1,3-benzodioxole 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 526-07-8 sesamolin 
• 16387-85-2 benzo[d][1,3]dioxol-5-yl 4-methylbenzenesulfonate 

Downstream Products

• 5451-82-1 piperidine-1-carboxylic acid benzo[1,3]dioxol-5-yl ester 
• 187987-86-6 6-((2-hydroxyphenyl)(4-morpholinyl)methyl)-1,3-benzodioxol-5-ol 
• 187987-85-5 6-[(2-hydroxy-3-methoxyphenyl)(4-morpholinyl)methyl]-1,3-benzodioxol-5-ol 
• 4720-68-7 4,5-methylenedioxy-2-hydroxybenzaldehyde 
• 105813-14-7 (3S,4R)-1-benzyl-4-(4-fluorophenyl)-3-[3,4-(methylenedioxy)-phenoxymethyl]piperidine 
• 918896-35-2 ethyl (3S)-hydroxy-3-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-2-(4-methylphenylsulfonyloxy)-(2R)-propionate 
• 66003-50-7 1-<4,5-(methylenedioxy)-2-hydroxyphenyl>ethanone 
• 93852-30-3 (Benzo[1,3]dioxol-5-yloxy)-phenyl-acetic acid ethyl ester 
• 96573-21-6 sesamyl β-methallylether 
• 147609-01-6 2,2',5'-trihydroxy-4,5-methylenedioxybiphenyl 

Relevant articles and documents

Design and synthesis of 3,4-methylenedioxy-6-nitrophenoxyacetylhydrazone derivatives obtained from natural safrole: New lead-agents with analgesic and antipyretic properties

In this work, we reported the synthesis and evaluation of the analgesic, anti-inflammatory, and antipyretic properties of new 2-(6-nitro-benzo[1,3]dioxol-5-yloxy)-acetylhydrazone derivatives (3), designed exploring molecular hybridization and isosteric replacement approaches between nimesulide (1) and carbanalogue NAH series (2) developed at LASSBio. Target compounds were synthesized in very good yields exploiting abundant Brazilian natural product safrole (4) as starting material. The evaluation of the antinociceptive properties of this series led us to discover a new potent prototype of analgesic and antipyretic agent, that is, NAH derivative 3c, named LASSBio-891, which showed to be more potent than dipyrone used as standard.

Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes

An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.

Synthesis process 3,4 -methylenedioxy phenol

The invention relates to the technical field of compound synthesis, in particular to a synthesis process of 3,4 -methylenedioxy phenol, which comprises the following steps: 3,4 - methylenedioxy acetophenone. The second Catalyst, first solvent was added to the autoclave, and an oxidant was added, and reacted 25 - 50 °C under 4 - 8h, and the first solvent was separated and the solvent was separated. The resulting 3,4 -methylenedioxy phenol acetate is obtained. The second Solvent, sodium hydroxide solution was added to the autoclave, and reacted 20 - 60 °C at 2 - 6h, adjusted pH to 3-6 to obtain 3,4 - methylenedioxy phenol. The method solves the problems that 3,4 -methylenedioxy acetophenone in the prior art is low in yield and large in separation difficulty in preparation of sesame phenol. The process takes the pepper ring as the starting raw material and is divided into three-step reaction synthesis, the raw material conversion rate is high, no other side reaction is avoided, the reaction condition is mild, the production cost is low, and the product quality is better.