3162-29-6

Basic information

• Product Name: 3,4-Methylenedioxyacetophenone
• Synonyms: 1-(1,3-Benzodioxol-5-yl)ethanone;3,4-Methylen-dioxy-acetophenon;TIMTEC-BB SBB007858;3',4'-(METHYLENEDIOXY)ACETOPHENONE;3,4-(METHYLENEDIOXY)ACETOPHENONE;3,4-METHYLENDIOXYACETOPHENONE;4-ACETYLMETHYLENEDIOXYBENZENE;5-ACETYL-1,3-BENZODIOXOLE
• CAS NO: 3162-29-6
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.16
• EINECS: 221-613-1
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Adehydes, Acetals & Ketones;C9;Carbonyl Compounds;Ketones
• Mol File: 3162-29-6.mol
• Article Data: 44

Chemical Properties

• Melting Point: 87-89 °C(lit.)
• Boiling Point: 152-155°C 15mm
• Flash Point: 152-155°C/15mm
• Appearance: Beige/Crystalline Powder
• Density: 1.2132 (rough estimate)
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: Store at RT.
• Water Solubility: Slightly soluble in water.
• BRN: 139669
• CAS DataBase Reference: 3,4-Methylenedioxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Methylenedioxyacetophenone(3162-29-6)
• EPA Substance Registry System: 3,4-Methylenedioxyacetophenone(3162-29-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 3162-29-6(Hazardous Substances Data)

Usage

Chemical Properties

BEIGE CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 3162-29-6 differently. You can refer to the following data:
1. 3?,4?-(Methylenedioxy)acetophenone is used in the synthesis of N-ethyl-1-(3,4-methylenedioxyphenyl)ethylamine.
2. 3′,4′-(Methylenedioxy)acetophenone was used in the synthesis of N-ethyl-1-(3,4-methylenedioxyphenyl)ethylamine.

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 4507, 1957 DOI: 10.1021/ja01573a069

Synthetic route

Methylenedioxybenzene (274-09-9) + acetic anhydride (108-24-7) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With trifluoroacetic acid at 20℃; for 1.5h; Friedel-Crafts Acylation;	98%
at 120℃; Friedel-Crafts Acylation;	90%
With diatomite-solid acid catalyst In 1,2-dichloro-ethane at 80℃; for 6h; Time; Friedel-Crafts Acylation;	90.3%

Methylenedioxybenzene (274-09-9) + acetic acid (64-19-7) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
In nitrobenzene at 80℃; Friedel-Crafts Acylation;	96%

1-benzo[1,3]dioxol-5-yl-ethanol (6329-73-3, 91613-73-9, 120523-14-0) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With 2,2'-bipyridinium chlorochromate In dichloromethane for 3.5h;	95%
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	84%
With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 80℃; Solvent; Time; Schlenk technique;	81%

1-benzo[1,3]dioxol-5-yl-ethylamine (121734-64-3) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With 4-phenylnaphthalene-1,2-dione In acetonitrile at 80℃; for 36h;	95%

Methylenedioxybenzene (274-09-9) + acetyl chloride (75-36-5) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With indium(III) tosylate In dodecane; nitromethane for 2.5h; Friedel-Crafts Acylation; Schlenk technique; Reflux;	94%
With 10percent AlCl3 on polystyrene In dichloromethane at 45℃; Friedel-Crafts Acylation;	94%
With diatomite-solid acid catalyst In 1,2-dichloro-ethane at 80℃; for 6h; Friedel-Crafts Acylation;	71.5%
With carbon disulfide; aluminium trichloride at -15℃;
With aluminum (III) chloride In dichloromethane at -50℃; for 2h; Friedel-Crafts Acylation; Sealed tube; Inert atmosphere;

methyl magnesium (1+); bromide + benzo[1,3]dioxole-5-carboxylic acid methoxymethylamide (147030-72-6) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	93%

isosafrole (120-58-1) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
Stage #1: isosafrole With N-iodo-succinimide; cetyltrimethylammonim bromide In 1,4-dioxane; water at 115℃; for 0.25h; Microwave irradiation; Stage #2: With dipyridinium dichromate; acetic acid In 1,4-dioxane; water at 115℃; for 0.25h; Microwave irradiation;	86%

methylmagnesium bromide (75-16-1) + benzo[1,3]dioxole-5-carboxylic acid methoxymethylamide (147030-72-6) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With benzotriazol-1-ol In tetrahydrofuran; diethyl ether at 0℃; for 1h;	85%

piperonal (120-57-0) + methylmagnesium bromide (75-16-1) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
Stage #1: piperonal; methylmagnesium bromide In tetrahydrofuran at 0℃; Green chemistry; Stage #2: With [bis(acetoxy)iodo]benzene at 0 - 20℃; Green chemistry;	80%

Methylenedioxybenzene (274-09-9) + Acetyl bromide (506-96-7) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With diatomite-solid acid catalyst In 1,2-dichloro-ethane at 80℃; for 6h; Friedel-Crafts Acylation;	76%

1-(benzo[d][1,3]dioxol-5-yl)-2,2-dibromoethan-1-one (783321-45-9) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + 1-(benzo[1,3]dioxol-5-yl)-2-bromoethanone (40288-65-1)

Conditions	Yield
With water; 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate at 125℃; under 2585.74 Torr; for 0.0416667h; microwave irradiation;	A n/a B 75%

S-2-(tert-butylcarbamoyl)phenyl ethanethioate (69672-52-2) + 3,4-(methylenedioxy)-benzeneboronic acid (94839-07-3) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With air; Cu(I)-3-methylsalicylate In N,N-dimethyl-formamide at 50℃; Miyaura-Suzuki reaction;	75%

1-(benzo[d][1,3]dioxol-5-yl)-2,2-dibromoethan-1-one (783321-45-9) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With water; 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate at 125℃; under 2585.74 Torr; for 0.116667h; microwave irradiation;	70%

5-(2,2-dibromovinyl)-1,3-benzodioxol (92449-54-2) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With water; zinc at 275℃; for 4h;	66%

diiodomethane (75-11-6) + 1-(3,4-dihydroxyphenyl)ethan-1-one (1197-09-7) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide Inert atmosphere;	65%

1-(2′-bromo-4′,5′-methylenedioxyphenyl)ethan-1-one (71095-26-6) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + 1-(6'-Acetyl-[5,5']bi[benzo[1,3]dioxolyl]-6-yl)-ethanone (79422-58-5)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0) In N,N-dimethyl-formamide 1.) - 78 deg C, 2.) 25 deg C, 10 min, 3.) 35 deg C, 12 h;	A 39% B 61%

4-(3,4-methylenedioxyphenyl)-4-oxo-2-(3,4,5-trimethoxyphenyl)butyramide (88775-41-1) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + (Z)-2-(3,4,5-trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenoic acid (88775-49-9) + 4-(3,4-methylenedioxyphenyl)-4-oxo-2-(3,4,5-trimethoxyphenyl)butyric acid (88775-29-5) + Eudesmic acid (118-41-2)

Conditions	Yield
With sodium hydroxide In ethanol for 10h; Product distribution; Heating; var. condition;	A 16% B 18.5% C 44.7% D 13.6%
With sodium hydroxide In ethanol for 10h; Heating;	A 0.227 g B n/a C n/a D n/a
With sodium hydroxide In ethanol for 6h; Heating;	A 0.021 g B 0.056 g C 0.14 g D 0.023 g

piperonal (120-57-0) + diazomethyl-trimethyl-silane (18107-18-1) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + safrole 2',3'-oxide (7470-44-2) + 1-(1,3-benzodioxol-5-yl)-2-propanone (4676-39-5)

Conditions	Yield
With triethylamine In methanol; diethyl ether for 24h; Ambient temperature;	A 19% B 9% C 37%
With triethylamine In methanol; dichloromethane for 24h; Ambient temperature;	A 17% B 14% C 34%

2-azido-1-(benzo[d][1,3]dioxol-5-yl)ethan-1-one (102831-07-2) → piperonal (120-57-0) + 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + benzo[1,3]dioxole-5-carboxylic acid (2-benzo[1,3]dioxol-5-yl-2-oxo-ethyl)amide

Conditions	Yield
In toluene Photolysis;	A 19% B 7% C 30%

diazomethane (186581-53-3, 908094-01-9) + piperonal (120-57-0) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With diethyl ether

3,4-(methylenedioxy)benzoyl chloride (25054-53-9) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With dimethylcadmium; benzene

(E)-1-(benzo[d][1,3]dioxol-5-yl)ethan-1-one oxime (62681-68-9) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With sulfuric acid

ethyl 3-(benzo[d][1,3]dioxol-5-yl)-3-oxopropanoate (81581-27-3) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With potassium hydroxide
With sulfuric acid

Methylenedioxybenzene (274-09-9) + acetyl chloride (75-36-5) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + diiodomethane (75-11-6) + dimethyl phthalate (635-67-6) + 3,4-diacetoxyacetophenone (72712-21-1)

Conditions	Yield
With sodium iodide In acetonitrile for 6h; Product distribution; Ambient temperature;	A n/a B 40 % Chromat. C 43 % Chromat. D n/a

4-acetoxy-3-methoxycarbonyl-4-(3,4-methylenedioxyphenyl)but-3-ene-2-one (104548-23-4) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating;
With sodium hydroxide In methanol for 2h; Heating;
With piperidine In methanol for 1h; Heating; further reagents: morpholine, piperazine;

methyllithium (917-54-4) + piperonylonitrile (4421-09-4) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78 - 20℃; for 2.5h;

piperonal (120-57-0) + methyl iodide (74-88-4) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With N-chloro-succinimide; magnesium 1.) C6H6, THF, 10 min, 2.) C6H6, THF, a) 0 deg C, 5 min, b) RT, 25 min; Yield given. Multistep reaction;

methylmagnesium chloride (676-58-4) + benzo[1,3]dioxole-5-carboxylic acid methoxymethylamide (147030-72-6) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
In tetrahydrofuran Substitution;

12-bromo-11-oxy-3.4-methylenedioxy-1-propyl-benzene → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6)

Conditions	Yield
With chromium(III) oxide; sulfuric acid

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → 1-(benzo[d][1,3]dioxol-5-yl)ethan-1-one oxime (62681-68-9)

Conditions	Yield
With hydroxylamine hydrochloride; triethylamine In ethanol for 25h;	100%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 95℃;	100%
With sodium hydroxide; hydroxylamine hydrochloride In ethanol; water at 25 - 80℃; Inert atmosphere;	87%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + (R)-2-methylpropane-2-sulfinamide (196929-78-9) → (R)-N-(1-(benzo[d][1,3]dioxol-5-yl)ethylidene)-2-methylpropane-2-sulfinamide

Conditions	Yield
With titanium(IV) tetraethanolate In tetrahydrofuran at 20℃; for 30h; Time; Reflux;	100%
With titanium(IV) tetraethanolate In tetrahydrofuran for 35.5h; Reflux;
With titanium (IV) ethoxide In tetrahydrofuran at 20℃; for 35.5h; Reflux;
With titanium(IV) tetraethanolate In tetrahydrofuran at 65℃; for 6h; Inert atmosphere;

3-thiophene carboxaldehyde (498-62-4) + 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → (E)-1-benzo[1,3]dioxol-5-yl-3-thiophen-3-ylpropenone

Conditions	Yield
Stage #1: 1-(benzo[d][1,3]dioxol-6-yl)ethanone With lithium hydroxide In ethanol at 20℃; for 0.166667h; Large scale; Stage #2: 3-thiophene carboxaldehyde In ethanol at 20℃; Large scale;	99%
With sodium hydroxide In ethanol; water

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → (R)-1-(benzo[d][1,3]dioxol-5-yl)ethan-1-ol (120523-14-0)

Conditions	Yield
With dimethylsulfide; dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane; toluene at 20℃; for 5h; Corey-Bakshi-Shibata reduction;	99%
With 1,1,1,3',3',3'-hexafluoro-propanol; C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; enantioselective reaction;	99%
With bromopentacarbonylmanganese(I); hydrogen; C45H43FeNP2; potassium hydroxide In methanol; toluene at 20℃; for 36h; enantioselective reaction;	99%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → (S)-1-[3,4-(methylenedioxy)phenyl]-1-ethanol (179237-91-3)

Conditions	Yield
With dimethylsulfide; dimethylsulfide borane complex; (R)-2-methyl-(CBS)-oxazaborolidine In dichloromethane; toluene at 20℃; for 5h;	99%
With dimethylsulfide; dimethylsulfide borane complex; (R)-2-methyl-CBS-oxaborolidine In dichloromethane; toluene at 20℃; for 5h; Corey-Bakshi-Shibata reduction;	99%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C53H73FeN2O2PS; hydrogen; lithium tert-butoxide In isopropyl alcohol at 25 - 30℃; under 22801.5 Torr; for 12h; Autoclave; enantioselective reaction;	99%
With Lactobacillus fermentum P1 whole cells at 26.44℃; for 30.39h; pH=6.2; pH-value; Temperature;	n/a

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + 5-(2-nitrophenyl)-2-furaldehyde (20000-96-8) → (2E)-1-(1',3'-benzodioxol-5-yl)-3-[5-(2-nitrophenyl)-furan-2-yl]-2-propen-1-one. (1352444-90-6)

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 24h; Aldol condensation;	99%
With potassium hydroxide In methanol; water at 20℃; for 24h; Aldol condensation;	99%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → 3,4-(methylenedioxy)phenyl methyl ketone-d6

Conditions	Yield
With 10% Pt/activated carbon; water-d2 In cyclohexane; isopropyl alcohol at 80℃; for 24h; Inert atmosphere;	99%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + 2-amino-1-benzylamine (4403-69-4) → Dubamine (6808-65-7)

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate); toluene-4-sulfonic acid In toluene at 100℃; for 36h; Schlenk technique; Sealed tube;	99%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + ethylene glycol (107-21-1) → C11H12O4

Conditions	Yield
With toluene-4-sulfonic acid In toluene; benzene at 110℃; for 20h; Dean-Stark;	99%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → 1-(3,4-methylenedioxyphenyl)-2-iodoethanone

Conditions	Yield
With iodine; copper(II) oxide In methanol for 1h; Heating;	98%
With iodine; Selectfluor In methanol at 22℃; for 26h;	75%
With iodine; copper(II) oxide In ethanol at 78℃;

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + 4-nitrobenzaldehdye (555-16-8) → 1-(benzo[d][1,3]dioxol-5-yl)-3-(4-nitrophenyl)prop-2-en-1-one

Conditions	Yield
Stage #1: 1-(benzo[d][1,3]dioxol-6-yl)ethanone With lithium hydroxide monohydrate In methanol at 20℃; for 1h; Stage #2: 4-nitrobenzaldehdye In methanol at 20℃; for 3h;	97.9%
With potassium hydroxide In methanol; water at 20℃;	79%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + thiosemicarbazide (79-19-6) → 1-(1,3-benzodioxol-5-yl)ethan-1-one thiosemicarbazone (18087-38-2)

Conditions	Yield
In ethanol for 4h; Reflux;	97%
Stage #1: 1-(benzo[d][1,3]dioxol-6-yl)ethanone With acetic acid In methanol for 0.25h; Reflux; Stage #2: thiosemicarbazide In methanol Reflux;

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → piperonal (120-57-0)

Conditions	Yield
With oxygen; copper(l) chloride In dimethyl sulfoxide at 120℃; under 60006 Torr;	97%

2-Aminobenzyl alcohol (5344-90-1) + 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → Dubamine (6808-65-7)

Conditions	Yield
With iron(III) oxide; potassium tert-butylate In toluene for 15h; Inert atmosphere; Sealed tube;	97%
With potassium tert-butylate; oxygen In toluene at 130℃; for 24h; Friedlaender Quinoline Synthesis; Green chemistry;	91%
With [(p-cymene)Ru(BiBzImH2)Cl][Cl]; caesium carbonate In tert-Amyl alcohol at 125℃; for 12h;	81%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + 2-iodobenzaldehyde (26260-02-6) → (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(2-iodophenyl)prop-2-en-1-one

Conditions	Yield
Stage #1: 1-(benzo[d][1,3]dioxol-6-yl)ethanone With sodium hydroxide In ethanol; water at 0℃; for 0.0833333h; Stage #2: 2-iodobenzaldehyde In ethanol; water at 0 - 10℃;	97%

5-bromo-2-furancarboxaldehyde (1899-24-7) + 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(5-bromofuran-2-yl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 16h; Claisen-Schmidt Condensation; Inert atmosphere; Microwave irradiation;	97%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + B-2-(2-methylallyl)-1,3,2-dioxaborinane (1433220-26-8) → 2-(benzo[d][1,3]dioxol-5-yl)-4-methylpent-4-en-2-ol (1433220-29-1)

Conditions	Yield
With tert-Amyl alcohol In neat (no solvent) at 23℃; Inert atmosphere;	96%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) → (S)-2-(benzo[d][1,3]dioxol-5-yl)pent-4-en-2-ol

Conditions	Yield
Stage #1: 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With (S)-2-((2-hydroxy-3-(triphenylsilyl)benzyl)amino)-3-methyl-1-(pyrrolidin-1-yl)butan-1-one; sodium t-butanolate In tetrahydrofuran; methanol; toluene at -30℃; for 0.5h; Inert atmosphere; Stage #2: 1-(benzo[d][1,3]dioxol-6-yl)ethanone In tetrahydrofuran; methanol; toluene at -30℃; for 8h; Inert atmosphere; enantioselective reaction;	96%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + (S)-2-methylpropane-2-sulfinamide (343338-28-3) → (E)-N-(1-(benzo[d][1,3]dioxol-5-yl)ethylidene)-2-methylpropane-2-sulfonamide

Conditions	Yield
Stage #1: 1-(benzo[d][1,3]dioxol-6-yl)ethanone; (S)-2-methylpropane-2-sulfinamide With titanium(IV) tetraethanolate In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 0.166667h; Inert atmosphere;	96%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + chloranil (118-75-2) → 5-acetyl-2-(4-hydroxy-2,3,5,6-tetrachlorophenoxy)-1,3-benzodioxole

Conditions	Yield
In benzene for 3h; Irradiation;	95%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → 1-benzo[1,3]dioxol-5-yl-ethanol (6329-73-3, 91613-73-9, 120523-14-0)

Conditions	Yield
With sodium tetrahydroborate In methanol; dichloromethane at 0℃; for 0.5h;	95%
With sodium tetrahydroborate; nickel(II) phthalocyanine In PEG-400 at 20℃; for 0.75h; chemoselective reaction;	95%
With C28H35ClCoN5(1+)*Cl(1-); potassium tert-butylate; hydrogen In tetrahydrofuran at 20℃; under 22502.3 Torr; for 16h; Autoclave;	92%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → 1-benzo[1,3]dioxol-5-yl-ethylamine (121734-64-3)

Conditions	Yield
Stage #1: 1-(benzo[d][1,3]dioxol-6-yl)ethanone With aluminium(III) triflate; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 1,2-bis-(diphenylphosphino)ethane In dodecane; toluene at -5℃; under 4500.45 Torr; for 0.5h; Autoclave; Stage #2: With hydrogen In dodecane; toluene at 140℃; under 30003 Torr; for 16h; Acidic conditions; chemoselective reaction;	95%
With 4-methoxy-N-(1-(naphthalen-2-yl)ethylidene)aniline; ammonium formate In methanol at 80℃; for 12h; Inert atmosphere; chemoselective reaction;	92%
With ammonia; hydrogen In tetrahydrofuran at 120℃; for 15h;	89%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + 2-chloro-6-methoxyquinolin-3-carboxaldehyde (73568-29-3) → (2E)-1-(1',3'-benzodioxol-5-yl)-3-(2-chloro-6-methoxyquinolin-3-yl)-2-propen-1-one (1352444-88-2)

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 24h; Aldol condensation;	95%
With potassium hydroxide In methanol; water at 20℃; for 24h; Aldol condensation;	95%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + 2,6-dimethoxybenzaldehyde (3392-97-0) → (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(2,6-dimethoxyphenyl)prop-2-en-1-one (1352444-80-4)

Conditions	Yield
Stage #1: 1-(benzo[d][1,3]dioxol-6-yl)ethanone With sodium hydroxide In ethanol; water at 20℃; for 0.0833333h; Claisen-Schmidt Condensation; Stage #2: 2,6-dimethoxybenzaldehyde at 20℃; Claisen-Schmidt Condensation;	95%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + [bromo(difluoro)methyl](trimethyl)silane (115262-01-6) → 1-(benzo[d][1,3]dioxol-5-yl)-2-fluoroprop-2-en-1-one

Conditions	Yield
Stage #1: 1-(benzo[d][1,3]dioxol-6-yl)ethanone; [bromo(difluoro)methyl]-trimethyl-silane With tetrabutylammomium bromide In toluene at 110℃; for 6h; Sealed tube; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 20℃; for 3h; Sealed tube;	95%

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + 4-methoxymethoxy-benzaldehyde (6515-21-5) → (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In methanol; water at 20℃; Claisen-Schmidt Condensation;	95%

Upstream product

• 186581-53-3 diazomethane 
• 120-57-0 piperonal 
• 6329-73-3 1-benzo[1,3]dioxol-5-yl-ethanol 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 62681-68-9 (E)-1-(benzo[d][1,3]dioxol-5-yl)ethan-1-one oxime 
• 676-58-4 methylmagnesium chloride 
• 147030-72-6 benzo[1,3]dioxole-5-carboxylic acid methoxymethylamide 
• 7647-01-0 hydrogenchloride 
• 57134-53-9 3,4-methylenedioxyphenylethyne 
• 7664-93-9 sulfuric acid 
• 81581-27-3 ethyl 3-(benzo[d][1,3]dioxol-5-yl)-3-oxopropanoate 
• 75-15-0 carbon disulfide 
• 274-09-9 Methylenedioxybenzene 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 59204-50-1 1-benzo[1,3]dioxol-5-yl-3-(2,4,6-trihydroxy-phenyl)-propenone 
• 110334-09-3 (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 58162-21-3 1-benzo[1,3]dioxol-5-yl-3-(2-hydroxy-phenyl)-propenone 
• 110420-63-8 (2E)-1-(1,3-benzodioxol-5-yl)-3-(3-methoxyphenyl)-2-propen-1-one 
• 94-53-1 Piperonylic acid 
• 62681-68-9 (E)-1-(benzo[d][1,3]dioxol-5-yl)ethan-1-one oxime 
• 40288-65-1 1-(benzo[1,3]dioxol-5-yl)-2-bromoethanone 
• 62396-98-9 benzo[1,3]dioxol-5-yl-oxo-acetic acid 
• 1197-09-7 1-(3,4-dihydroxyphenyl)ethan-1-one 
• 56136-84-6 methyl 3,4-(methylenedioxy)-6-nitrophenyl ketone 
• 88775-45-5 (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one 
• 76530-89-7 1,3-bis-benzo[1,3]dioxol-5-ylpropenone 
• 170570-78-2 1-(1,3-benzodioxol-5-yl)-4,4-difluorobutane-1,3-dione 
• 95-54-5 1,2-diamino-benzene 

Relevant articles and documents

AN EFFICIENT PROCESS FOR PREPARATION OF ACYL DERIVATIVES OF ALKYLENEDIOXYBENZENES

The present disclosure provides a process of preparation of compounds of Formula I comprising the step of : reacting an alkylenedioxybenzene compound of Formula II with an acyl halide of Formula III in presence of a solvent, wherein the step of reacting the alkylenedioxybenzene compound of Formula II with the acyl halide of Formula III is effected in presence of an amphoteric oxide and a Lewis acid so as to immediately quench the compound of formula H-X, formed during the course of the reaction, to substantially eliminate degradation of the compound of any of Formula I and II. The present disclosure also provides for process(es) for preparation of compound of Formula IVa, IVb and IVc.

Scalable Aerobic Oxidation of Alcohols Using Catalytic DDQ/HNO3

A selective, practical, and scalable aerobic oxidation of alcohols is described that uses catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and HNO3, with molecular oxygen serving as the terminal oxidant. The method was successfully applied to the oxidation of a wide range of benzylic, propargylic, and allylic alcohols, including two natural products, namely, carveol and podophyllotoxin. The conditions are also applicable to the selective oxidative deprotection of p-methoxybenzyl ethers.

Facile preparation of 5-alkyl-1-aryltetrazoles with arenes, acyl chlorides, hydroxylamine, and diphenylphosphoryl azide

Successive treatment of arenes with acyl chlorides and AlCl3, the addition of water and removal of solvent, the reaction with NH2OH?HCl and K2CO3, and the reaction with diphenylphosphoryl azide and DBU under warming conditions gave the corresponding 5-alkyl-1-aryltetrazoles efficiently in good to moderate yields. The present method is one-pot transformation of arenes into 5-alkyl-1-aryltetrazoles using the Friedel-Crafts acylation and the Beckmann rearrangement under transition-metal-free conditions.