104-01-8

Basic information

• Product Name: 4-Methoxyphenylacetic acid
• Synonyms: ASISCHEM D13364;LABOTEST-BB LT00848110;HOMOANISIC ACID;HOMO-P-ANISIC ACID;4-METHOXYPHENYLACETIC ACID;P-METHOXY-A-CARBOXYTOLUENE;P-METHOXYPHENYLACETIC ACID;RARECHEM AL BO 0133
• CAS NO: 104-01-8
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 203-166-4
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;pharmacetical;Building Blocks;C9;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;Pyridines
• Mol File: 104-01-8.mol
• Article Data: 114

Chemical Properties

• Melting Point: 84-86 °C(lit.)
• Boiling Point: 140 °C3 mm Hg(lit.)
• Flash Point: 193°C
• Appearance: White to light yellow/Crystalline Powder and Chunks
• Density: 1.1708 (rough estimate)
• Vapor Pressure: 0.143mmHg at 25°C
• Refractive Index: 1.5101 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 6g/l
• PKA: pK1:4.358 (25°C)
• Water Solubility: 6 g/L (20 ºC)
• BRN: 1101737
• CAS DataBase Reference: 4-Methoxyphenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxyphenylacetic acid(104-01-8)
• EPA Substance Registry System: 4-Methoxyphenylacetic acid(104-01-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: AI8960000
• TSCA: Yes
• Hazardous Substances Data: 104-01-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 104-01-8 differently. You can refer to the following data:
1. 4-Methoxyphenylacetic Acid is a compound that was found from microbial phenolic metabolites in human feces after the consumption of gin, red wine and dealcholized red wine.
2. Preparation of pharmaceuticals, other organic compounds.
3. 4-Methoxyphenylacetic acid can be used:To prepare methyl 4-methoxyphenylacetate by esterification with dimethyl carbonate using mesoporous sulfated zirconia catalyst.As a ligand to synthesize pharmacologically important dinuclear gallium(III) and phenyltin(IV) carboxylate metal complexes.As a reactant to synthesize hydroxylated (E)-stilbenes by reacting with substituted benzaldehydes via Perkin reaction.

Description

4-METHOXYPHENYLACETIC ACID(104-01-8) is used in organic synthesis as well as pharmaceutical industry, especially used as an intermediate of puerarin. It can also be used as potential plasma biomarkers for early detection of non-small cell lung cancer. It is also used in drug industry as an intermediate to make Dextromethorphan.

Reference

Chen, Yan Ping, Y. M. Chen, and M. Tang. "Solubilities of cinnamic acid, phenoxyacetic acid and 4-methoxyphenylacetic acid in supercritical carbon dioxide." Fluid Phase Equilibria 275.1(2008):33-38.

Chemical Properties

white to light yellow crystalline powder and

Definition

ChEBI: A monocarboxylic acid that is phenylacetic acid carrying a 4-methoxy substituent. It is used as an intermediate for pharmaceuticals and other organic synthesis. It has been found to inhibit the germination of cress and lettuce seeds.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 4354, 1986 DOI: 10.1021/jo00373a005Tetrahedron Letters, 35, p. 133, 1994 DOI: 10.1016/0040-4039(94)88182-0

General Description

Pale yellow or off white colored flakes. Severely irritates skin and eyes. May be toxic by ingestion.

Reactivity Profile

Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in 4-Methoxyphenylacetic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise the acid from EtOH/water, EtOAc/pet ether (m 87o) or *C6H6/pet ether (m 84-86o). [Beilstein 10 III 431, 10 IV 544.] The acid chloride [4693-91-8] has M 184.6, b 143o/10mm, d 254

InChI:InChI=1/C8H8O3/c1-10-7-2-4-8(5-3-7)11-6-9/h2-6H,1H3

Synthetic route

2-(4-Methoxyphenyl)ethanol (702-23-8) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite In acetonitrile at 35℃; pH 6.7;	100%
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; water; acetonitrile at 35℃; pH=6.7; Reagent/catalyst; Green chemistry;	100%
With periodic acid; pyridinium chlorochromate In acetonitrile	99%

4-Methoxymandelic acid (20714-90-3) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With hydrogenchloride; palladium on activated charcoal; hydrogen; acetic acid at 60℃; for 2h; Reagent/catalyst; Temperature;	99.1%

2-(4-methoxyphenyl)-1-(pyrrolidin-1-yl)ethan-1-one (123902-08-9) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 36h; Heating;	99%

4-methoxysalicylaldehyde (52289-54-0) + ethylene glycol (107-21-1) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
Stage #1: 4-methoxysalicylaldehyde; ethylene glycol With sodium nitrate; aluminum isopropoxide at 47℃; for 1.5h; Stage #2: With cobalt(II) chloride at 56℃; for 3h; Temperature;	98.9%

N-[(E)-1-Cyano-2-(4-methoxy-phenyl)-vinyl]-4,N-dimethyl-benzamide (89244-17-7, 89244-18-8) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 6h; Heating;	96%

p-methoxybenzyl chloride (824-94-2) + butan-1-ol (71-36-3) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
Stage #1: butan-1-ol With cobalt(II) sulfate at 80℃; under 3750.38 Torr; for 4h; Autoclave; Stage #2: p-methoxybenzyl chloride With sodium hydroxide In water at 80℃; under 3750.38 Torr; for 24h; Concentration; Pressure; Temperature; Autoclave;	93.6%

4-methoxy-phenyl acetic acid methyl ester (23786-14-3) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With sodium hydroxide for 2h; Heating;	93%
With sodium hydroxide In methanol for 4h; Ambient temperature;	92%
With potassium carbonate; thiophenol In 1-methyl-pyrrolidin-2-one at 190℃; for 0.166667h; Substitution;	80%

(4-methoxy-phenyl)-acetic acid-(4-nitro-benzyl ester) (133430-48-5) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With zinc In tetrahydrofuran for 3.5h; Ambient temperature;	93%
	92.6%

ethyl p-methoxyphenylacetate (14062-18-1) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With sodium hydroxide In methanol for 4h; Ambient temperature;	92%
With water; sodium hydroxide In 1,4-dioxane at 60℃; for 2h; pH=10 - 14;	91%
Stage #1: ethyl p-methoxyphenylacetate With water; sodium hydroxide In methanol at 20℃; for 1h; Stage #2: With hydrogenchloride In water	67%
With potassium hydroxide

2,2,2-trichloro-1-(4-methoxyphenyl)ethan-1-ol (14337-31-6) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
Stage #1: 2,2,2-trichloro-1-(4-methoxyphenyl)ethan-1-ol With sodium tetrahydroborate; diphenyl diselenide In ethanol Inert atmosphere; Stage #2: With sodium hydroxide In ethanol at 40℃; Inert atmosphere;	92%

(E)-2-Amino-3-(4-methoxy-phenyl)-acrylonitrile (154199-04-9) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With sodium hydroxide In methanol for 1.5h; Ambient temperature;	90%

p-methoxybenzoylformic acid (7099-91-4) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
Stage #1: p-methoxybenzoylformic acid With sodium iodide In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With chloro-trimethyl-silane In dichloromethane at 20℃; for 2h; Inert atmosphere; regioselective reaction;	90%

α-(N-Methylanilino)-p-methoxycinnamonitrile (91668-55-2) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 8h; Heating;	89%

p-methoxybenzylnitrile (104-47-2) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With water; sodium hydroxide In ethanol Reflux;	87.1%
With potassium phosphate buffer at 30℃; for 19h; Rhodococcus sp. AJ270 cells;	85.5%
With potassium hydroxide

2-diazo-1-(4-methoxyphenyl)ethanone (6832-17-3) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With lithium perchlorate; silver; silver(l) oxide In water; acetonitrile at 26.85℃; Wolff rearrangement; Electrochemical reaction;	87%
With lithium perchlorate In acetonitrile at 26.85℃; Wolff rearrangement; Electrochemical reaction;	86%

1-(2,2-dibromovinyl)-4-methoxybenzene (60512-57-4) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With PEG-400; sodium hydroxide; bis[1,2-bis(diphenylphosphino)ethane]palladium(0) In dichloromethane at 60 - 65℃; for 17h;	85%
With triethylsilane; cyclohexa-1,4-diene; water; oxygen; cobalt acetylacetonate In tetrahydrofuran; nonane at 24℃; under 760.051 Torr; for 12h; Reagent/catalyst;	71%

4-methoxy-N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)phenylglycinonitrile → 4-Methoxyphenylacetic acid (104-01-8) + N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)amine (888963-33-5)

Conditions	Yield
With hydrogen bromide; acetic acid In dichloromethane; water at 20℃; for 2h;	A 85% B n/a

4-Methylanisole (104-93-8) + carbon dioxide (124-38-9) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With bis(2-pyridyl)methane; xanth-9-one; nickel(II) chloride hexahydrate; potassium tert-butylate In benzene at 20℃; under 760.051 Torr; for 4h; Reagent/catalyst; Irradiation; Schlenk technique;	84%

2-(4-methoxyphenyl)-2-((4-methylphenyl)sulfonamido)acetic acid → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With sodium tetrahydroborate; trifluoroacetic acid In dichloromethane at 15 - 25℃;	83%

4-methoxyphenylacetylen (768-60-5) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With 4-methylpyridine-1-oxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; water; P(p-C6H4F)3 In acetonitrile at 60℃; for 8h; chemoselective reaction;	82%
Stage #1: 4-methoxyphenylacetylen With 1-methyl-pyrrolidin-2-one; C17H11ClF6N2Ru(1+) In water at 25℃; for 24h; Inert atmosphere; Stage #2: With [bis(acetoxy)iodo]benzene at 25℃; for 1h;	82%
Multi-step reaction with 3 steps 1: (i) NaNH2, (ii) sulfur, (iii) /BRN= 969135/ 2: HgO, aq. H2SO4 3: aq. H2SO4 / Heating View Scheme
Stage #1: 4-methoxyphenylacetylen With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 2h; Stage #3: With oxone In acetone at 50℃; for 12h;
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 °C / Inert atmosphere 2.1: oxone||potassium monopersulfate triple salt; water / acetone / 12 h / 50 °C / Inert atmosphere View Scheme

carbon dioxide (124-38-9) + p-Methoxybenzyl bromide (2746-25-0) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With samarium; chloro-trimethyl-silane; tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; under 760.051 Torr; for 2h; Electrochemical reaction; Cooling with ice;	80%

4-hydroxyphenylacetate (156-38-7) + dimethyl sulfate (77-78-1) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With sodium hydroxide In water at 40 - 45℃; for 12h;	76%
With sodium hydroxide
Stage #1: 4-hydroxyphenylacetate; dimethyl sulfate With sodium hydroxide In methanol; water at 20℃; Stage #2: With hydrogenchloride In methanol; water pH=2 - 3;

carbon monoxide (201230-82-2) + p-Methoxybenzyl bromide (2746-25-0) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With palladium hydroxide, 20 wt% on carbon; tetrabutylammomium bromide; water In tetrahydrofuran at 110℃; under 7500.75 Torr; for 4h; Sealed tube; Autoclave;	76%

trifluorormethanesulfonic acid (1493-13-6) + silver trifluoromethanesulfonate (2923-28-6) + 2-Bromo-4'-methoxyacetophenone (2632-13-5) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
In methanol	75%

formic acid (64-18-6) + p-methoxybenzyl chloride (824-94-2) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; palladium diacetate In N,N-dimethyl-formamide at 115℃; for 12h; Inert atmosphere;	73%

4-methoxy-benzaldehyde (123-11-5) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
Stage #1: 4-methoxy-benzaldehyde With tetrabutylammomium bromide; water; sodium hydroxide In chloroform at 60℃; for 4.5h; Inert atmosphere; Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate at 80℃; for 3h;	71%
Multi-step reaction with 2 steps 1: 89 percent / KH / tetrahydrofuran / 5 h / Ambient temperature 2: 89 percent / 10percent aq. HCl / tetrahydrofuran / 8 h / Heating View Scheme
Multi-step reaction with 2 steps 1: potassium cyanide; aqueous hydrochloric acid / Einleiten von Chlorwasserstoff in eine methanol. Loesung des erhaltenen Nitrils und Behandeln des danach isolierten Reaktionsprodukts mit Wasser 2: palladium; hydrogen bromide / Hydrogenation.Behandlung des Reaktionsprodukts mit heisser wss. Natronlauge View Scheme
Multi-step reaction with 2 steps 1: triphenylphosphine / dichloromethane / 4 h / 0 °C 2: cobalt acetylacetonate; cyclohexa-1,4-diene; triethylsilane; oxygen; water / tetrahydrofuran; nonane / 12 h / 24 °C / 760.05 Torr View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide / tetrahydrofuran / 10 h / 20 °C / Green chemistry 2: boron trifluoride diethyl etherate; water / 1,4-dioxane / 0.5 h / 175 °C / Microwave irradiation; Green chemistry View Scheme

carbon dioxide (124-38-9) + p-methoxybenzyl chloride (824-94-2) → 4-Methoxyphenylacetic acid (104-01-8)

Conditions	Yield
With (1,2-dimethoxyethane)dichloronickel(II); C15H27P*(x)BF4*H(1+); magnesium chloride; zinc In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; Schlenk technique;	70%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; manganese; palladium diacetate; magnesium chloride In N,N-dimethyl-formamide under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique;	68%
With samarium; chloro-trimethyl-silane; tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; under 760.051 Torr; for 2h; Electrochemical reaction; Cooling with ice;	50%
With magnesium 1.) THF, 20 deg C, 30 min, 2.) THF, from 10 deg C to 25 deg C, 1.5 h; Yield given. Multistep reaction;
Stage #1: p-methoxybenzyl chloride With magnesium; lithium chloride; zinc(II) chloride In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran at 25℃; for 2h;	326 mg

2-(4-methoxyphenyl)acetophenone (24845-40-7) → 4-Methoxyphenylacetic acid (104-01-8) + 4-methoxybenzil (22711-21-3)

Conditions	Yield
With oxygen; copper diacetate; triphenylphosphine In o-xylene at 100℃; for 4h; Reagent/catalyst; Temperature; Time;	A 70% B 24%
With oxygen; copper dichloride In o-xylene at 130℃; for 5.5h; Time; Reagent/catalyst;	A 8% B 50%

carbon dioxide (124-38-9) + p-methoxybenzyl chloride (824-94-2) → 4-Methoxyphenylacetic acid (104-01-8) + 4-Methylanisole (104-93-8)

Conditions	Yield
With salcomine; tetrabutylammonium perchlorate; water In acetonitrile at 25℃; electrochemical reaction;	A 8.2% B 64%
With salcomine; tetrabutylammonium perchlorate In acetonitrile at 25℃; electrochemical reaction;	A 38% B 37.6%
With tetraethylammonium perchlorate In acetonitrile at 25℃; Electrochemical reaction;

4-Methoxyphenylacetic acid (104-01-8) → 4-methoxyphenyl-acetic chloride (4693-91-8)

Conditions	Yield
With thionyl chloride In toluene Heating;	100%
With thionyl chloride In dichloromethane	100%
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 23℃;	100%

4-Methoxyphenylacetic acid (104-01-8) + phenethylamine (64-04-0) → 2-(4-methoxyphenyl)-N-(2-phenylethyl)acetamide (83304-16-9)

Conditions	Yield
With 4-methyl-morpholine; triazine-type dehydrocondensing polymer In dichloromethane at 20℃; for 19h;	100%
With 4-methyl-morpholine; polymeric triazine reagent In dichloromethane at 20℃; for 19h;	100%
In neat (no solvent) at 150℃; for 0.5h; Microwave irradiation;	99%

methanol (67-56-1) + 4-Methoxyphenylacetic acid (104-01-8) → 4-methoxy-phenyl acetic acid methyl ester (23786-14-3)

Conditions	Yield
With hydrogenchloride for 1h; Heating;	100%
With hydrogenchloride for 3h; Heating;	100%
With thionyl chloride at 0 - 20℃; for 1.5h;	99%

4-Methoxyphenylacetic acid (104-01-8) → 2-(4-Methoxyphenyl)ethanol (702-23-8)

Conditions	Yield
With borane In tetrahydrofuran Ambient temperature;	100%
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃;	98.3%
With tricarbonyl(η(4)-cycloocta-1,5-diene)iron; phenylsilane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; UV-irradiation; chemoselective reaction;	95%

4-Methoxyphenylacetic acid (104-01-8) + allyl bromide (106-95-6) → 2-(4-methoxyphenyl)-4-pentenoic acid (51230-91-2)

Conditions	Yield
Stage #1: 4-Methoxyphenylacetic acid With ethylmagnesium chloride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 0.5h; Reagent/catalyst; Temperature; Inert atmosphere;	100%
Stage #1: 4-Methoxyphenylacetic acid With sodium hydride In tetrahydrofuran for 2h; Heating / reflux; Stage #2: With lithium diisopropyl amide In tetrahydrofuran at 10 - 20℃; for 2h; Stage #3: allyl bromide In tetrahydrofuran at 20 - 45℃;	93%
With n-butyllithium 1.) a) THF, 0 deg C, 1 h, b) RT, 2 h, 2.) a) THF, HMPA, 0 deg C, 1 h, b) RT, 4 h; Yield given. Multistep reaction;
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium 1.) THF, 2.) THF, from 0 deg C to RT, 5 h; Yield given. Multistep reaction;

4-Methoxyphenylacetic acid (104-01-8) + (S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2) → 4-Methoxyphenylacetic acid (S)-(-)-2'-hydroxy-1,1'-binaphthyl-2-yl ester (124931-82-4, 132353-54-9)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 4h; Ambient temperature;	100%

4-Methoxyphenylacetic acid (104-01-8) + 2,4-dimethoxylbenzyl alcohol (7314-44-5) → 2,4-dimethoxybenzyl 4-methoxyphenylacetate (258875-95-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Esterification;	100%

phenylacetic acid (103-82-2) + 3-dimethylamino-1-(4-methylphenyl)propanamine (917351-49-6) + 4-Methoxyphenylacetic acid (104-01-8) + (E)-3-phenylacrylic acid (140-10-3) + 3-(4-methoxyphenyl)propanoic acid (1929-29-9) + (E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) + 4-Trifluoromethylphenylacetic acid (32857-62-8) + 3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid (2062-26-2, 87212-84-8, 16642-92-5) + 3-(4-trifluoromethylphenyl)propionic acid (53473-36-2) + phenylpropyolic acid (637-44-5) + 3-Phenylpropionic acid (501-52-0) → N-[3-dimethylamino-1-(4-methylphenyl)propyl]cinnamic amide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-3-phenylpropiolic amide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-2-phenylacetamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-2-(4-trifluoromethylphenyl)acetamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-2-(4-methoxyphenyl)acetamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-3-phenylpropionamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-3-(4-trifluoromethylphenyl)propionamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-3-(4-methoxyphenyl)propionamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-4-(trifluoromethyl)cinnamamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-4-methoxycinnamamide

Conditions	Yield
With polyvinylpyridine polymer-supported dimethylaminopyridine; PS-carbodiimide In dichloromethane at 20℃; for 96h; Polystyrene;	A 100% B 100% C 93% D 98% E 93% F 96% G 78% H 98% I 56% J 87%

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phenylacetic acid (103-82-2) + 3-dimethylamino-1-(2-naphthyl)propanamine (917351-50-9) + 4-Methoxyphenylacetic acid (104-01-8) + (E)-3-phenylacrylic acid (140-10-3) + 3-(4-methoxyphenyl)propanoic acid (1929-29-9) + (E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) + 4-Trifluoromethylphenylacetic acid (32857-62-8) + 3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid (2062-26-2, 87212-84-8, 16642-92-5) + 3-(4-trifluoromethylphenyl)propionic acid (53473-36-2) + phenylpropyolic acid (637-44-5) + 3-Phenylpropionic acid (501-52-0) → N-[3-dimethylamino-1-(2-naphthyl)propyl]-2-(4-trifluoromethylphenyl)acetamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-2-(4-methoxyphenyl)acetamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-2-phenylacetamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-3-phenylpropionamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-3-(4-trifluoromethylphenyl)propionamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-3-(4-methoxyphenyl)propionamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]cinnamamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-4-(trifluoromethyl)cinnamamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-4-methoxycinnamamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-3-phenylpropiolamide

Conditions	Yield
With polyvinylpyridine polymer-supported dimethylaminopyridine; PS-carbodiimide In dichloromethane at 20℃; for 96h; Polystyrene;	A 88% B 79% C 67% D 66% E 84% F 94% G 76% H 100% I 100% J 100%

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1-(4-chlorophenyl)-N3,N3-dimethylpropane-1,3-diamine (885672-69-5) + phenylacetic acid (103-82-2) + 4-Methoxyphenylacetic acid (104-01-8) + (E)-3-phenylacrylic acid (140-10-3) + 3-(4-methoxyphenyl)propanoic acid (1929-29-9) + (E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) + 4-Trifluoromethylphenylacetic acid (32857-62-8) + 3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid (2062-26-2, 87212-84-8, 16642-92-5) + 3-(4-trifluoromethylphenyl)propionic acid (53473-36-2) + phenylpropyolic acid (637-44-5) + 3-Phenylpropionic acid (501-52-0) → N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-2-phenylacetamide (885673-16-5) + N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-2-(4-trifluoromethylphenyl)acetamide + N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-2-(4-methoxyphenyl)acetamide + N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-3-phenylpropionamide + N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-3-(4-trifluoromethylphenyl)propionamide + N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-3-(4-methoxyphenyl)propionamide + N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]cinnamamide + N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-4-(trifluoromethyl)cinnamamide + N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-4-methoxycinnamamide + N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-3-phenylpropiolamide

Conditions	Yield
With polyvinylpyridine polymer-supported dimethylaminopyridine; PS-carbodiimide In dichloromethane at 20℃; for 96h; Polystyrene;	A 92% B 96% C 96% D 92% E 83% F 81% G 83% H 97% I 83% J 100%

...Expand

4-Methoxyphenylacetic acid (104-01-8) + ethyl acrylate (140-88-5) → C19H22O7

Conditions	Yield
With N-(tert-butyloxycarbonyl)-L-isoleucine; oxygen; palladium diacetate; p-benzoquinone In tert-Amyl alcohol at 85℃; under 760.051 Torr; for 48h;	100%

4-Methoxyphenylacetic acid (104-01-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N,N-dimethyl-2-(4-methoxyphenyl)ethanamide (19625-79-7)

Conditions	Yield
With sulfur trioxide pyridine complex In 1,2-dichloro-benzene at 160℃; Schlenk technique; Inert atmosphere;	100%
With tert.-butylhydroperoxide; copper(II) perchlorate hexahydrate at 100℃; for 6h;	78%

4-Methoxyphenylacetic acid (104-01-8) + (R)-benzyl 2-amino-4-methylpentanoate hydrochloride (68838-94-8) → N-(p-methoxylphenylacetyl)-D-leucine benzyl ester (1374963-36-6)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 5.33333h; Inert atmosphere;	100%
With benzotriazol-1-ol

4-Methoxyphenylacetic acid (104-01-8) + 1,3-benzodioxol-5-ylmethyl amine (2620-50-0) + 4-oxo-benzaldehyde (1185185-57-2) + tert-butylisonitrile (119072-55-8, 7188-38-7) → C29H30N2O6

Conditions	Yield
Stage #1: 1,3-benzodioxol-5-ylmethyl amine; 4-oxo-benzaldehyde In methanol at 60℃; for 0.0833333h; Ugi Condensation; Microwave irradiation; Stage #2: 4-Methoxyphenylacetic acid; tert-butylisonitrile In methanol at 60℃; for 3h; Ugi Condensation; Microwave irradiation;	100%

4-Methoxyphenylacetic acid (104-01-8) + methyl iodide (74-88-4) → 4-methoxy-phenyl acetic acid methyl ester (23786-14-3)

Conditions	Yield
With potassium carbonate In acetone at 60℃;	100%
With potassium carbonate In acetone at 60℃;	100%

4-Methoxyphenylacetic acid (104-01-8) + ethanol (64-17-5) → ethyl p-methoxyphenylacetate (14062-18-1)

Conditions	Yield
With toluene-4-sulfonic acid for 2h; Reflux; Inert atmosphere;	99%
With acetyl chloride at 50℃; for 1.5h;	97%
With hydrogenchloride for 20h;	96%

4-Methoxyphenylacetic acid (104-01-8) → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With boron tribromide In dichloromethane at -78 - -15℃; for 4h; Inert atmosphere;	99%
With boron tribromide In dichloromethane at -78℃; for 0.5h;	93%
With hydrogen bromide; cetyltributylphosphonium bromide for 7.5h; Heating;	87%

4-Methoxyphenylacetic acid (104-01-8) + benzylamine (100-46-9) → N-benzyl-2-(4-methoxyphenyl)acetamide (52532-96-4)

Conditions	Yield
With (2-(thiophen-2-ylmethyl)phenyl)boronic acid In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve;	99%
With zirconium(IV) chloride In toluene at 110℃; for 5h; Inert atmosphere; sealed tube;	91%
Stage #1: 4-Methoxyphenylacetic acid With N-chlorobenzotriazole; triphenylphosphine In dichloromethane for 0.25h; Stage #2: benzylamine With triethylamine In dichloromethane at 20℃; for 2h;	91%

4-Methoxyphenylacetic acid (104-01-8) + benzyl bromide (100-39-0) → benzyl 2-(4-methoxyphenyl)ethanoate (74587-15-8)

Conditions	Yield
With potassium carbonate In acetone Heating;	99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	4.44 g

(6-formyl-naphthalen-2-yloxy)-acetic acid tert-butyl ester (270082-18-3) + 4-Methoxyphenylacetic acid (104-01-8) + Cyclohexyl isocyanide (931-53-3) + 4-methoxy-benzylamine (2393-23-9) → [6-(cyclohexylcarbamoyl-{(4-methoxy-benzyl)-[(4-methoxy-phenyl)-acetyl]-amino}-methyl)-naphthalen-2-yloxy]-acetic acid tert-butyl ester

Conditions	Yield
In methanol for 24h; Ugi reaction; Heating;	99%

(6-formyl-naphthalen-2-yloxy)-acetic acid tert-butyl ester (270082-18-3) + 4-Methoxyphenylacetic acid (104-01-8) + Benzyl isocyanide (88333-03-3, 10340-91-7) + 4-methoxy-benzylamine (2393-23-9) → [6-(benzylcarbamoyl-{(4-methoxy-benzyl)-[(4-methoxy-phenyl)-acetyl]-amino}-methyl)-naphthalen-2-yloxy]-acetic acid tert-butyl ester

Conditions	Yield
In methanol for 24h; Ugi reaction; Heating;	99%

4-Methoxyphenylacetic acid (104-01-8) + 4-Methoxyphenethylamine (55-81-2) → 2-(4-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide (41898-71-9)

Conditions	Yield
In neat (no solvent) at 150℃; for 0.5h; Microwave irradiation;	99%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine

4-Methoxyphenylacetic acid (104-01-8) + 4-chlorophenylethylamine (156-41-2) → N-[2-(4-chlorophenyl)ethyl]-2-(4-methoxyphenyl)acetamide (925124-73-8)

Conditions	Yield
In neat (no solvent) at 150℃; for 0.5h; Microwave irradiation;	99%

4-Methoxyphenylacetic acid (104-01-8) + 2-(2-(trifluoromethyl)phenyl)ethan-1-amine (774-18-5) → 2-(4-methoxyphenyl)-N-{2-[2-(trifluoromethyl)phenyl]ethyl}acetamide (1439537-71-9)

Conditions	Yield
In neat (no solvent) at 150℃; for 0.5h; Microwave irradiation;	99%

4-Methoxyphenylacetic acid (104-01-8) + (E)-but-2-enol (504-61-0) → (E)-crotyl p-methoxyphenylacetate (1626423-89-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 23℃; for 0.5h;	99%

4-Methoxyphenylacetic acid (104-01-8) + diethylzinc (557-20-0) → 1-(4-methoxyphenyl)butan-2-one (53917-01-4)

Conditions	Yield
Stage #1: 4-Methoxyphenylacetic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 1.5h; Stage #2: diethylzinc With tetrakis(triphenylphosphine) palladium(0) In hexane; benzene at 0 - 20℃; for 15h; Negishi Coupling;	99%

4-Methoxyphenylacetic acid (104-01-8) + (R)-1-phenyl-ethyl-amine (3886-69-9) → (R)-2-(4-methoxyphenyl)-N-(1-phenylethyl)acetamide

Conditions	Yield
With (2-(thiophen-2-ylmethyl)phenyl)boronic acid In dichloromethane at 20℃; for 8h; Inert atmosphere; Molecular sieve;	99%

Upstream product

• 140-67-0 Estragole 
• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 13305-14-1 methyl 2-hydroxy-2-(4-methoxyphenyl)acetate 
• 64-19-7 acetic acid 
• 491-80-5 5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 124-38-9 carbon dioxide 
• 824-94-2 p-methoxybenzyl chloride 
• 104-93-8 p-methylanizole 
• 34086-51-6 4',7-dimethoxy-5-hydroxyisoflavone 
• 98470-01-0 5-hydroxy-7-methoxy-3-(4-methoxy-phenyl)-6-methyl-chromen-4-one 
• 104-47-2 p-methoxybenzylnitrile 
• 487-49-0 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 7722-84-1 dihydrogen peroxide 

Downstream Products

• 4705-34-4 1,2-bis(4-methoxyphenyl)ethene 
• 83307-72-6 E-methyl-3-(2-furyl)-(2-p-methoxyphenyl) acrylic acid 
• 14062-18-1 ethyl p-methoxyphenylacetate 
• 857564-80-8 3,6-dihydroxy-2,4,4'-trimethoxy-deoxybenzoin 
• 22110-04-9 6-hydroxy-2,3,4-trimethoxyphenyl p-methoxybenzyl ketone 
• 149091-24-7 (4-methoxy-phenyl)-acetic acid-(2-dimethylamino-ethyl ester) 
• 13721-20-5 2-(3-chloro-4-methoxyphenyl)acetic acid 
• 156-38-7 4-hydroxyphenylacetate 
• 95540-82-2 meso-2,3-bis-(4-methoxy-phenyl)-succinic acid 
• 96122-61-1 2-(3-iodo-4-methoxyphenyl)acetic acid 
• 63304-80-3 (4-methoxy-3-nitrophenyl)acetic acid 
• 104967-35-3 (3-chlorosulfonyl-4-methoxy-phenyl)-acetic acid 
• 20341-24-6 (4-methoxy-phenyl)-acetic acid-(3-methoxy-phenethylamide) 
• 4693-91-8 4-methoxyphenyl-acetic chloride 

Relevant articles and documents

Wolff rearrangement of α-diazoketones using in situ generated silver nanoclusters as electron mediators

We report Wolff rearrangement of α-diazoketones by in situ generated silver nanoclusters (Agn, 2-4 nm) from silver(I) oxide (Ag 2O) involving a nonclassical electron-transfer process. Our results show that Agn+/Agn0 redox couple allows the initial removal of an electron from α-diazoketone and its back-donation after chemical reaction(s). Controlled potential coulometry (CPC) of various α-diazoketones results in the realization of Wolff-rearranged carboxylic acids in excellent yields.

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Silver nanocluster redox-couple-promoted nonclassical electron transfer: An efficient electrochemical wolff rearrangement of α-diazoketones

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Copper-catalyzed oxidation of deoxybenzoins to benzils under aerobic conditions

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