591-31-1

Basic information

• Product Name: 3-Methoxybenzaldehyde
• Synonyms: 3-methoxybenzaldehde;3-methoxy-benzaldehyd;Metamethoxybenzaldehyde;M-METHOXYBENZALDEHYDE;AKOS BBS-00003247;3-ANISALDEHYDE;3-METHOXYBENZALDEHYDE;META-ANISALDEHYDE
• CAS NO: 591-31-1
• Molecular Formula: C₈H₈O₂
• Molecular Weight: 136.14792
• EINECS: 209-712-8
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Building Blocks;C8;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;aldehyde;Pyridines
• Mol File: 591-31-1.mol
• Article Data: 339

Chemical Properties

• Melting Point: 187 °C
• Boiling Point: 143 °C50 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear pale yellow to yellow/Liquid
• Density: 1.117 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0647mmHg at 25°C
• Refractive Index: n20/D 1.553(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol (Slightly)
• Water Solubility: insoluble
• Sensitive: Air Sensitive
• BRN: 606013
• CAS DataBase Reference: 3-Methoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxybenzaldehyde(591-31-1)
• EPA Substance Registry System: 3-Methoxybenzaldehyde(591-31-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: BZ2605000
• F: 9-23
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 591-31-1(Hazardous Substances Data)

Usage

Chemical Properties

clear pale yellow to yellow liquid

Uses

3-Methoxybenzaldehyde is used to prepare 3-(3-methoxy-phenyl)-1-phenyl-propenone by reaction with benzldehyde. It is used as an eluent for mono-13C isotopomers of vanillin in normal phase silica gel chromatography. It acts as an inhibitor of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism.

Synthesis Reference(s)

Synthetic Communications, 24, p. 2011, 1994 DOI: 10.1080/00397919408010209

General Description

m-Anisaldehyde has significant antifungal activity against Candida sp., including the azole-resistant strains.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits acrid smoke andirritating vapors.

Purification Methods

Wash it with saturated aqueous NaHCO3, then H2O, dry it with anhydrous MgSO4 and distil it under reduced pressure under N2. Store it under N2 in sealed glass ampoules. [Beilstein 8 IV 241.]

InChI:InChI=1/C8H8O2/c1-10-8-4-2-3-7(5-8)6-9/h2-6H,1H3

Synthetic route

3-methoxybenzyl alcohol (6971-51-3) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With oxygen; perruthenate modified mesoporous silicate MCM-41 In toluene at 80℃; for 3h; Oxidation;	100%
With Oxone; [Mn(NO3)2(2,3,5,6-tetra(2-pyridyl)pyrazine)(H2O)]; tetrabutylammomium bromide In dichloromethane at 20℃; Catalytic behavior; Reagent/catalyst;	100%
With 1-benzyl-1-aza-4-azoniabicyclo<2.2.2>octane periodate In acetonitrile for 10h; Heating;	99%

1,1-diacetoxy-1-(3-methoxyphenyl)methane (59184-17-7) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With sulphated zirconia In acetonitrile at 60℃; for 1h; Microwave irradiation;	100%
With (NH4)3PW12O40 In methanol at 20℃; for 1h;	93%
With poly(4-vinylpyridinium) hydrogen sulfate solid acid In methanol at 20℃; for 0.966667h; Irradiation;	92%

m-anisoyl chloride (1711-05-3) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With polymethylhydrosiloxane; trifuran-2-yl-phosphane; tetrabutyl ammonium fluoride; potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water at 20℃; for 1h;	98%
With palladium; xylene at 140 - 150℃; Hydrogenation;
With sodium tris(tert-butoxo)aluminium hydride In tetrahydrofuran; diethylene glycol dimethyl ether at -78℃; for 3h; Yield given;
Stage #1: m-anisoyl chloride With aluminium hydride In tetrahydrofuran at 20℃; for 1h; Metallation; Stage #2: With pyridinium chlorochromate In tetrahydrofuran; dichloromethane at 20℃; for 3h; Oxidation;	97 % Chromat.

(3-Methoxy-benzyloxy)-trimethyl-silane (132816-03-6) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With aluminium trichloride; tetramethylammonium chlorochromate In acetonitrile for 1.08333h; Heating;	98%
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.166667h; Heating;	96%
With aluminium trichloride; benzyltriphenylphosphonium chlorochromate In acetonitrile for 0.75h; Heating;	95%

3-methoxybenzaldehyde phenylhydrazone → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.1h; Heating;	98%
With quinolinium monofluorochromate(VI) In dichloromethane at 20℃; for 0.8h;	93%
With cetyltrimethylammonium peroxodisulphate In acetonitrile for 0.333333h; Reflux;	93%

m-methoxybenzyl chloride (824-98-6) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With water; sodium hydroxide at 20℃; for 0.05h; Microwave irradiation;	98%
With 4-methylmorpholine N-oxide; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride; potassium iodide at 100℃; for 0.0333333h; Microwave irradiation; Ionic liquid;	92%
With sodium nitrate; acetic acid In water for 7.5h; Reflux;	81%

N-tert-butyl-1-(3-methoxyphenyl)methanimine (82632-37-9) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
Stage #1: N-tert-butyl-1-(3-methoxyphenyl)methanimine With chromium dichloride In tetrahydrofuran at 25℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: With phenylmagnesium bromide In tetrahydrofuran at 25℃; for 5h; Schlenk technique; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 25℃; for 3h; Schlenk technique; Inert atmosphere; regioselective reaction;	98%
With water

3-methoxyphenyl bromide (2398-37-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
Stage #1: 3-methoxyphenyl bromide With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 1h; Further stages.;	96%
Ambient temperature; Mg anode, Cd coated catode, Bu4NBr electrolyte;	56%
Stage #1: 3-methoxyphenyl bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 0℃;

2-(3-methoxyphenyl)-1,3-dioxolane (19693-78-8) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate In dichloromethane for 0.05h; Irradiation;	96%
With aluminium trichloride; 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate for 0.00833333h;	96%
With 2,6-dicarboxypyridinium chlorochromate In acetonitrile at 20℃; for 0.25h;	94%
With potassium dichromate; aluminium trichloride for 0.0833333h;	90%
With K5 In acetone for 0.166667h; Heating;	97 % Chromat.

carbon monoxide (201230-82-2) + 3-methoxyphenyl sulfurofluoridate → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With pyridine; 1,3-bis-(diphenylphosphino)propane; hydrogen; palladium diacetate In dimethyl sulfoxide at 120℃; under 7500.75 Torr; for 2h; Flow reactor;	96%

3-methoxybenzaldehyde oxime (38489-80-4) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With aluminium trichloride; benzyltriphenylphosphonium chlorochromate In acetonitrile for 0.666667h; Heating;	95%
With potassium permanganate; 1-n-butyl-3-methylimidazolim bromide at 20℃; for 0.7h; Ionic liquid; chemoselective reaction;	94%
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 0.666667h; Heating;	90%

2-[(3-methoxyphenyl)methylene]hydrazinecarboxamide → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With NTPPPODS In water; acetonitrile for 0.25h; Reflux;	95%
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.166667h; Heating;	94%
With quinolinium monofluorochromate(VI) In acetonitrile for 3h; Heating;	93%

(E)-1-(3-methoxyphenyl)-N-phenylmethanimine (17637-72-8) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With hydrogenchloride; water In diethyl ether; toluene at 20℃; for 2h; Inert atmosphere;	95%

C15H16N2O4S (1448723-38-3) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
Stage #1: C15H16N2O4S With 1H-imidazole; 1-(Trimethylsilyl)imidazole In toluene at 55℃; McFadyen-Stevens Reaction; Stage #2: With citric acid In methanol at 20℃; McFadyen-Stevens Reaction;	95%
Stage #1: C15H16N2O4S With 1H-imidazole; 1-(Trimethylsilyl)imidazole In toluene at 55℃; Inert atmosphere; Stage #2: With citric acid In toluene at 23℃; Inert atmosphere;	95%

1-Methoxy-3-phenethyloxymethyl-benzene (121336-27-4) → 2-phenylethanol (60-12-8) + 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 24h;	A 80% B 94%

3-methoxylbenzyl azide (123767-44-2) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With iron(III) chloride; dihydrogen peroxide In dichloromethane; water for 13h; Reflux; Air;	94%

meta-hydroxybenzaldehyde (100-83-4) + methyl iodide (74-88-4) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25 - 30℃; for 12h; Inert atmosphere;	93%
With potassium carbonate In acetone for 3h; Reflux;	92%
With potassium carbonate In N,N-dimethyl-formamide	91%

formic acid (64-18-6) + 3-methoxy-1-iodobenzene (766-85-8) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With dicyclohexyl-carbodiimide; sodium phosphate at 105℃; for 3h; Green chemistry;	93%
With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; dicyclohexyl-carbodiimide at 100℃; for 2h; Sealed tube;	85%
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 2h; Sealed tube;	80%
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube;	79%

2-(3-methoxyphenyl)-1,3-dithiane (54308-43-9) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
Stage #1: 2-(3-methoxyphenyl)-1,3-dithiane With trichloroisocyanuric acid; silica gel at 20℃; for 0.05h; Stage #2: With water at 20℃;	92%
With p-benzoquinone; sodium iodide In water; acetonitrile at 100℃; for 24h;	91%
With eosin y In water; acetonitrile at 20℃; for 2h; Irradiation;	91%
With tetrachlorosilane; dimethyl sulfoxide In dichloromethane at 20℃; for 0.75h;	90%
With water In 1,4-dioxane at 100℃; for 48h; Inert atmosphere;	74%

1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-octane-1-sulfonic acid 4-formyl-2-methoxy-phenyl ester (689247-71-0) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With formic acid; potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; acetone; toluene at 100℃; for 0.333333h; microwave irradiation;	92%

2-(3-methoxy-phenyl)-[1,3]oxathiolane → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With Iron(III) nitrate nonahydrate at 90℃; for 0.133333h;	92%

ethyl 3-methoxythiobenzoate (28145-59-7) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With triethylsilane; palladium on activated charcoal In acetone at 20℃;	91%
With triethylsilane; palladium on activated charcoal In tetrahydrofuran at 20℃; for 5h; Fukuyama reduction;	90%
With triethylsilane; palladium on activated charcoal In acetone Ambient temperature; Yield given;

3-methoxystyrene (626-20-0) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With eosin Y; oxygen In dimethyl sulfoxide at 20℃; for 9h; Irradiation; Green chemistry;	91%
With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen In 1,2-dichloro-ethane at 70℃; under 760.051 Torr; for 6h; Green chemistry; chemoselective reaction;	78%

meta-hydroxybenzaldehyde (100-83-4) + dimethyl sulfate (77-78-1) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With potassium carbonate In acetone for 0.0833333h; Etherification; methylation; microwave irradiation;	90%
With sodium hydroxide
With sodium hydroxide

2-(3-methoxybenzyloxy)tetrahydro-2H-pyran (18483-97-1) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With dipotassium peroxodisulfate; molybdenum trioxide In water; acetonitrile for 0.34h; Reflux;	90%
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 0.5h; Heating;	88%
With aluminium trichloride; benzyltriphenylphosphonium chlorochromate In acetonitrile for 0.5h; Heating;	88%

sodium; hydroxy-(3-methoxy-phenyl)-methanesulfonate → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With Montmorillonite KSF clay for 0.00277778h; Elimination; microwave irradiation;	90%

1-(3-Methoxyphenyl)ethanone (586-37-8) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With copper(l) iodide; oxygen In dimethyl sulfoxide at 120℃; for 26h; chemoselective reaction;	90%

5-[(3-methoxyphenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione (6258-45-3) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With oxone In water; acetonitrile at 45℃; for 1h;	90%

N-(2-cyanoethyl) N-(3-methoxybenzyl)-4-methylaniline (127598-74-7) → 3-(2-Dimethylaminomethyl-4-methyl-phenylamino)-propionitrile (118072-35-8) + 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With water; trichlorophosphate In N,N-dimethyl-formamide Vilsmeier reaction;	A 80% B 89%

2-(4-methoxyphenyl)-1,3-dithiane (24588-72-5) → 3-methoxy-benzaldehyde (591-31-1)

Conditions	Yield
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 3h; Heating;	89%

3-methoxy-benzaldehyde (591-31-1) + methylamine (74-89-5) → N-(3-methoxybenzylidene)methanamine (16928-30-6)

Conditions	Yield
at 20℃; for 12h;	100%
In ethanol at 0 - 40℃;	90%
In water for 10h; Ambient temperature;	86%

3-methoxy-benzaldehyde (591-31-1) → 3-methoxybenzyl alcohol (6971-51-3)

Conditions	Yield
With hydrogen; Pd as electrode electrochemical reaction;	100%
With sodium tetrahydroborate In methanol at 20℃; for 1h;	100%
With sodium tetrahydroborate; Dowex1-x8 In tetrahydrofuran at 20℃; for 0.5h;	99%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 3-methoxy-benzaldehyde (591-31-1) → ethyl (E)-3-(3-methoxyphenyl)acrylate (33877-04-2, 24393-55-3)

Conditions	Yield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With lithium chloride In tetrahydrofuran at 20℃; for 0.25h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Stage #2: 3-methoxy-benzaldehyde With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Horner-Wadsworth-Emmons Olefination; Inert atmosphere;	100%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h;	100%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 30℃; for 4h; Glovebox;	98%

3-methoxyphenyl bromide (2398-37-0) + 3-methoxy-benzaldehyde (591-31-1) → bis(3-methoxyphenyl)methanol (55360-45-7)

Conditions	Yield
With n-butyllithium In hexane; ethyl acetate	100%
With magnesium In diethyl ether for 1h; Ambient temperature;	62%
With magnesium 1.) ether, ultrasound; Yield given. Multistep reaction;
Stage #1: 3-methoxyphenyl bromide With magnesium In tetrahydrofuran at 0℃; Reflux; Inert atmosphere; Stage #2: 3-methoxy-benzaldehyde In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran
Stage #1: 3-methoxyphenyl bromide With magnesium In diethyl ether at 20℃; for 2h; Inert atmosphere; Stage #2: 3-methoxy-benzaldehyde In diethyl ether at 20℃; for 2h; Inert atmosphere;

carbon tetrabromide (558-13-4) + 3-methoxy-benzaldehyde (591-31-1) → 1,1-dibromo-2-(3-methoxyphenyl)ethene (253684-23-0)

Conditions	Yield
With triphenylphosphine In dichloromethane	100%
With triphenylphosphine In dichloromethane at 0℃; for 5.25h; Inert atmosphere;	96%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: 3-methoxy-benzaldehyde In dichloromethane at 0℃; for 1.08333h; Inert atmosphere;	94%

potassium cyanide (151-50-8) + 3-methoxy-benzaldehyde (591-31-1) → m-methoxymandelonitrile (53313-94-3)

Conditions	Yield
Stage #1: 3-methoxy-benzaldehyde With hydrogenchloride; sodium sulfite In tetrahydrofuran; water at 20℃; for 0.166667h; Stage #2: potassium cyanide In tetrahydrofuran; water for 0.5h;	100%
With sodium hydrogensulfite 1) H2O, 40 deg C, 0.5 h, 2) H2O, 0 deg C, 1 h; Multistep reaction;
With acetic acid In water
With hydrogenchloride; sodium sulfite In tetrahydrofuran at 20℃; for 0.5h;

3-methoxy-benzaldehyde (591-31-1) + acetone (67-64-1) → (E)-4-(3-methoxyphenyl)but-3-en-2-one (20766-31-8, 30625-53-7)

Conditions	Yield
With sodium hydroxide In water at 0 - 25℃; for 5h;	100%
With 1-n-butyl-3-methylimidazolim bromide at 60℃; for 6h; Aldol condensation; Enzymatic reaction;	87%
With sodium hydroxide for 1.66667h;	83%

3-methoxy-benzaldehyde (591-31-1) + methylamine (74-89-5) → 1-(3-methoxyphenyl)-N-methylmethanamine (41789-95-1)

Conditions	Yield
With sodium tetrahydroborate In methanol; water at 0℃; for 2h;	100%
With sodium tetrahydroborate In methanol; water at 0 - 20℃;	99%
Stage #1: 3-methoxy-benzaldehyde; methylamine In methanol; water at 0 - 20℃; for 15.3333h; Stage #2: With sodium tetrahydroborate In methanol; 20C at 0 - 20℃; for 2 - 3h; Product distribution / selectivity;	29%

3-methoxy-benzaldehyde (591-31-1) + toluene-4-sulfonic acid hydrazide (1576-35-8) → N'-(3-methoxybenzylidene)-4-methylbenzen sulfonohydrazide (19350-71-1)

Conditions	Yield
In ethanol for 8h; Reflux;	100%
With polystyrene sulfonic acid In water at 100℃; for 0.0833333h; Wavelength; Reagent/catalyst; Solvent; Temperature; Microwave irradiation; Green chemistry;	92%
In methanol at 20℃; for 3h;	90%

diethylzinc (557-20-0) + 3-methoxy-benzaldehyde (591-31-1) → (1S)-1-(3-methoxyphenyl)propan-1-ol (134677-28-4)

Conditions	Yield
(1S)-1-(9-piperidylfluoren-9-yl)ethanol In hexane; toluene at 0℃; for 4h; Addition;	100%
Stage #1: diethylzinc In toluene at 0℃; for 0.5h; Stage #2: 3-methoxy-benzaldehyde In toluene at 0 - 20℃; for 48h; Reagent/catalyst; enantioselective reaction;	99%
With (3S,4S)-2,2-dimethyl-4-[N-(9'-phenylfluoren-9'-yl)amino]pentan-3-ol In hexane; toluene at 18℃; for 1h; Addition;	97%

diethylzinc (557-20-0) + 3-methoxy-benzaldehyde (591-31-1) → 1-(3-methoxyphenyl)propanol (52956-27-1)

Conditions	Yield
With (R,R)-(2,4,6-Me3C6H2-CH=N-CH(Ph))2; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane 1.) -78 deg C, 4 h, 2.) -20 deg, 1 h;	100%
With (1R,2R)-N,N'-bis[(2,4,6-trimethylphenyl)methylene]-1,2-cyclohexane-diamine; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane at -78 - -20℃; for 5h;	100%
Stage #1: diethylzinc With titanium(IV) isopropylate; (1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol In hexane; dichloromethane at 25℃; for 0.333333h; Inert atmosphere; Stage #2: 3-methoxy-benzaldehyde In hexane; dichloromethane at 0℃; for 24h; Reagent/catalyst; Inert atmosphere;	53%

3-methoxy-benzaldehyde (591-31-1) + trimethyl orthoformate (149-73-5) → m-anisaldehyde dimethyl acetal (59276-28-7)

Conditions	Yield
In methanol at 20℃; for 1h; Inert atmosphere;	100%
With ytterbium(III) chloride hexahydrate In methanol at 20℃; for 18h;	98%
With toluene-4-sulfonic acid In methanol at 20℃; for 1h; Inert atmosphere; Sealed tube;	93%

(R)-2-methoxy-1-phenylethylamine (64715-85-1, 91298-74-7, 127180-88-5) + 3-methoxy-benzaldehyde (591-31-1) → ((R)-2-Methoxy-1-phenyl-ethyl)-[1-(3-methoxy-phenyl)-meth-(E)-ylidene]-amine

Conditions	Yield
In toluene Heating;	100%

3-methoxy-benzaldehyde (591-31-1) + Ethyl isobutyrate (97-62-1) → ethyl 3-hydroxy-3-(3-methoxyphenyl)-2,2-dimethylpropanoate (602304-70-1, 293769-53-6)

Conditions	Yield
Stage #1: Ethyl isobutyrate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 3-methoxy-benzaldehyde In tetrahydrofuran at -78℃; for 1.5h;	100%

3-methoxy-benzaldehyde (591-31-1) + ethyl cyanoformate (623-49-4) → (2S)-O-ethoxycarbonyl-2-hydroxy-2-(3-methoxyphenyl)-acetonitrile

Conditions	Yield
With potassium cyanide; 18-crown-6 ether; chiral salen-based titanium In dichloromethane at -40℃; for 24h;	100%
With 3,3'-di-naphthalen-2-yl-biphenyl-2,2'-diol; titanium(IV) isopropylate; quinindine; isopropyl alcohol In toluene at -20℃; for 7h; Strecker reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%
With chiral [(salen)TiO]2 In dichloromethane at -40℃; for 17h;	94%
With chiral bimetallic titanium(salen) In dichloromethane at -40℃; for 17h;	94%
With potassium cyanide; 18-crown-6 ether; titanium(salen) complex In dichloromethane at -40℃; for 24h;

4-hydroxy[1]benzopyran-2-one (1076-38-6) + 3-methoxy-benzaldehyde (591-31-1) → 3,3'-((3-methoxyphenyl)methylene)bis(4-hydroxy-2H-chromen-2-one) (10172-74-4)

Conditions	Yield
With 4-sulfophthalic acid In water at 80℃; for 0.333333h; Catalytic behavior; Green chemistry;	100%
With piperidine In ethanol at 20℃; for 4h;	98%
With 4-aminobenzene sulfonic acid In water at 80℃; for 0.366667h; Green chemistry;	96%

3-methoxy-benzaldehyde (591-31-1) + 1-amino-2-propene (107-11-9) → N-[(3-methoxyphenyl)methylidene]-N-(2-propenyl)amine (246509-60-4)

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 20h;	100%
With magnesium sulfate In dichloromethane for 1h; Heating;	95%

potassium cyanide + 3-methoxy-benzaldehyde (591-31-1) → m-methoxymandelonitrile (53313-94-3)

Conditions	Yield
With hydrogenchloride; sodium sulfite In tetrahydrofuran; water at 20℃; for 0.666667h;	100%

butane-2,3-dione mono-oxime (135636-66-7) + 3-methoxy-benzaldehyde (591-31-1) → 2-(3-methoxy-phenyl)-4,5-dimethyl-oxazole-3-oxide

Conditions	Yield
Stage #1: butane-2,3-dione mono-oxime; 3-methoxy-benzaldehyde With hydrogenchloride; acetic acid In toluene at 22℃; for 16h; Stage #2: With sodium hydroxide In water; toluene at 32℃; pH=10.6;	100%

tert-butyl 1-(2-methylallyl)hydrazinecarboxylate (1005794-49-9) + 3-methoxy-benzaldehyde (591-31-1) → tert-butyl 2-(3-methoxybenzylidene)-1-(2-methylallyl)hydrazinecarboxylate

Conditions	Yield
In ethanol at 20℃;	100%

tert-butylamine (75-64-9) + 3-methoxy-benzaldehyde (591-31-1) → N-tert-butyl-1-(3-methoxyphenyl)methanimine (82632-37-9)

Conditions	Yield
In dichloromethane at 20℃; for 4h;	100%
With titanium tetrachloride In diethyl ether; toluene at 0℃; for 0.25h; Glovebox; Inert atmosphere; Schlenk technique;	93%
at 100℃; for 4h;	86%

dimethyl <2-(tert-butyldimethylsilyl)-2-oxoethyl>-phosphonate (120943-70-6) + 3-methoxy-benzaldehyde (591-31-1) → (E)-1-(tert-butyldimethylsilyl)-3-(3-methoxyphenyl)prop-2-en-1-one (1204324-78-6)

Conditions	Yield
Stage #1: dimethyl <2-(tert-butyldimethylsilyl)-2-oxoethyl>-phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; Horner-Wadsworth-Emmons olefination; Inert atmosphere; Stage #2: 3-methoxy-benzaldehyde In tetrahydrofuran at 20℃; for 15h; Horner-Wadsworth-Emmons olefination; Inert atmosphere;	100%

trimethylsilyl cyanide (7677-24-9) + 3-methoxy-benzaldehyde (591-31-1) → C12H17NO2Si

Conditions	Yield
Stage #1: trimethylsilyl cyanide; 3-methoxy-benzaldehyde; (S,S,S)-[Ru(2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl)bis(phenylglycinate)] In tetrahydrofuran; tert-butyl methyl ether at -78℃; for 0.166667h; Inert atmosphere; Stage #2: lithium chloride In tetrahydrofuran; tert-butyl methyl ether at -78℃; for 3h; Product distribution / selectivity; Inert atmosphere;	100%

3-methoxy-benzaldehyde (591-31-1) + 4-methoxycarbonyl aniline (619-45-4) → 4-[(3-methoxy-benzylidene) amino]-benzoic acid methyl ester (349456-93-5)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 12h; Reflux;	100%
In N,N-dimethyl-formamide at 100 - 150℃;

N-(4-chlorophenyl)-2,2-dimethylpropionamide (65854-91-3) + 3-methoxy-benzaldehyde (591-31-1) → N-{4-chloro-2-[hydroxy(3-methoxyphenyl)methyl]-phenyl}-2,2-dimethylpropanamide (1292850-39-5)

Conditions	Yield
Stage #1: N-(4-chlorophenyl)-2,2-dimethylpropionamide With sec.-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 2h; Stage #2: 3-methoxy-benzaldehyde In tetrahydrofuran; hexane at 0℃; for 0.5h;	100%

3-methoxy-benzaldehyde (591-31-1) → [(3-methoxyphenyl)methylidene]hydrazine (108087-83-8)

Conditions	Yield
With hydrazine hydrate In ethanol at 20℃; Cooling;	100%
With hydrazine hydrate In methanol at 20℃; for 1h;	99%
With hydrazine hydrate In methanol at 20℃; for 1h;	99%

trimethylsilyl cyanide (7677-24-9) + 3-methoxy-benzaldehyde (591-31-1) + methylamine (74-89-5) → 2-(3-methoxyphenyl)-2-(methylamino)acetonitrile

Conditions	Yield
Stage #1: 3-methoxy-benzaldehyde; methylamine In methanol; water for 1h; Stage #2: trimethylsilyl cyanide In methanol; water at 20℃; for 24h;	100%

3-methoxy-benzaldehyde (591-31-1) + p-aminoethylbenzoate (94-09-7) → 4-[(3-methoxy-benzylidene) amino]-benzoic acid methyl ester (349456-93-5)

Conditions	Yield
toluene-4-sulfonic acid In toluene for 12h; Reflux;	100%

Upstream product

• 1711-05-3 m-anisoyl chloride 
• 1899-02-1 trimethylphenylammonium hydroxide 
• 100-83-4 meta-hydroxybenzaldehyde 
• 80-48-8 methyl p-toluene sulfonate 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 5071-96-5 3-METHOXYBENZYLAMINE 
• 578-58-5 2-methylmethoxybenzene 
• 766-85-8 3-methoxy-1-iodobenzene 
• 201230-82-2 carbon monoxide 
• 64-19-7 acetic acid 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 100-66-3 methoxybenzene 
• 4885-02-3 Dichloromethyl methyl ether 

Downstream Products

• 71972-47-9 (E)-3-(3-methoxybenzylidene)chroman-4-one 
• 110420-63-8 (2E)-1-(1,3-benzodioxol-5-yl)-3-(3-methoxyphenyl)-2-propen-1-one 
• 81625-24-3 cyano(3-methoxyphenyl)methyl ethyl carbonate 
• 56005-42-6 (E)-2-(3-methoxy-phenylmethylene)-cyclohexanone 
• 6099-04-3 3-methoxycinnamic acid 
• 34000-28-7 2'-hydroxy-3-methoxy-chalcone 
• 91098-97-4 benzoic acid-(3-methoxy-benzylidenehydrazide) 
• 61190-04-3 (3-methoxy-benzylidenamino)-acetaldehyde diethylacetal 
• 65152-37-6 4t-(3-methoxy-phenyl)-2-oxo-but-3-enoic acid 
• 55606-43-4 3-methoxy-benzaldehyde-(N-benzyl oxime ) 
• 110117-34-5 E-2-(3'-methoxybenzylidene)-1-indanone 
• 54671-37-3 3-methoxy-benzaldehyde (5,5-dimethyl-4-oxo-oxazolidin-2-ylidene)-hydrazone 
• 76784-48-0 9-(3-Methoxybenzyliden)-6,7,8,9-tetrahydro-5H-cycloheptapyridin 
• 125208-20-0 4-[(E)-2-(3-Methoxy-phenyl)-vinyl]-5,5-dimethyl-2-oxo-2,5-dihydro-furan-3-carbonitrile 

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