4693-91-8

Basic information

• Product Name: 4-METHOXYPHENYLACETYL CHLORIDE
• Synonyms: 4-METHOXYPHENYLACETYL CHLORIDE;4-METHOXYBENZENEACETYL CHLORIDE;4-METHOXYPHENYLACETYL CHLORIDE 98%;p-Methoxyphenylacetyl chloride;4-Methoxyphenylacetyl chloride,98%;4-Methoxyphenacetyl chloride;p-Anisylacetyl chloride;p-Methoxyphenacetyl chloride
• CAS NO: 4693-91-8
• Molecular Formula: C₉H₉ClO₂
• Molecular Weight: 184.62
• EINECS: -0
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 4693-91-8.mol
• Article Data: 111

Chemical Properties

• Boiling Point: 143 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear light yellow/Liquid
• Density: 1.208 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00387mmHg at 25°C
• Refractive Index: n20/D 1.54(lit.)
• Storage Temp.: 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 908061
• CAS DataBase Reference: 4-METHOXYPHENYLACETYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXYPHENYLACETYL CHLORIDE(4693-91-8)
• EPA Substance Registry System: 4-METHOXYPHENYLACETYL CHLORIDE(4693-91-8)

Safety Data

• Hazard Codes: C
• Statements: 14-34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 8-10
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 4693-91-8(Hazardous Substances Data)

Usage

Chemical Properties

clear light yellow liquid

Uses

4-Methoxyphenylacetyl chloride may be used in the synthesis of:substituted spiro[4.5]decane1-(4′-hydroxybenzyl)-6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline (higenamine), a cardiotonic principle of aconite root2,5-naphthyridine(R)-(+)-nor-roefractine

InChI:InChI=1/C9H9ClO2/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3

Synthetic route

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%

p-Methoxybenzyl bromide (2746-25-0) → 4-methoxyphenyl-acetic chloride (4693-91-8) + di-p-tolyl cadmium

Conditions	Yield
Multi-step reaction with 3 steps 1: AcOH; aq. NaOH 2: thionyl chloride View Scheme

p-methoxybenzylnitrile (104-47-2) → 4-methoxyphenyl-acetic chloride (4693-91-8) + di-p-tolyl cadmium

Conditions	Yield
Multi-step reaction with 2 steps 1: AcOH; aq. NaOH 2: thionyl chloride View Scheme

4-Methoxybenzyl alcohol (105-13-5) → 4-methoxyphenyl-acetic chloride (4693-91-8) + di-p-tolyl cadmium

Conditions	Yield
Multi-step reaction with 4 steps 1: PBr3 / CH2Cl2 2: AcOH; aq. NaOH 3: thionyl chloride View Scheme

1-methyl-pyrrolidin-2-one (872-50-4) + 4-Methoxyphenylacetic acid (104-01-8) → 4-methoxyphenyl-acetic chloride (4693-91-8)

Conditions	Yield
With thionyl chloride

4-hydroxyphenylacetate (156-38-7) → 4-methoxyphenyl-acetic chloride (4693-91-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 12 h / 40 - 45 °C 2: thionyl chloride / 5 h / 60 °C View Scheme

4-Methoxyphenylacetic acid (104-01-8) + chloroacetyl chloride (79-04-9) → 4-methoxyphenyl-acetic chloride (4693-91-8)

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide at 30℃; for 2h; Inert atmosphere;

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + 4-methoxyphenyl-acetic chloride (4693-91-8) → N-methoxy-2-(4-methoxyphenyl)-N-methylethanamide (267884-96-8)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1h;	100%
With pyridine In dichloromethane at 20℃; for 1h;	88%
With pyridine; dmap; sodium hydrogencarbonate In diethyl ether
With pyridine In dichloromethane at 0℃; for 1h;

(S)-9-Trityloxy-nonan-4-ol (401788-86-1) + 4-methoxyphenyl-acetic chloride (4693-91-8) → (4-Methoxy-phenyl)-acetic acid (S)-1-propyl-6-trityloxy-hexyl ester

Conditions	Yield
With potassium tert-butylate; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide	100%

2-hydroxy-5-nitroaniline (99-57-0) + 4-methoxyphenyl-acetic chloride (4693-91-8) → N-(2-hydroxy-5-nitro-phenyl)-2-(4-methoxy-phenyl)-acetamide

Conditions	Yield
With pyridine In tetrahydrofuran at 0 - 20℃; for 2h;	100%

3-bromo-N-methylaniline (66584-32-5) + 4-methoxyphenyl-acetic chloride (4693-91-8) → N-(3-bromophenyl)-2-(4-methoxyphenyl)-N-methylacetamide (1268826-67-0)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%

methoxybenzene (100-66-3) + 4-methoxyphenyl-acetic chloride (4693-91-8) → 1,4-di(4-methoxyphenyl)ethanone (120-44-5)

Conditions	Yield
With aluminum (III) chloride at 25℃; for 0.75h; Friedel-Crafts Acylation; Cooling;	99%
With aluminum (III) chloride In dichloromethane at 20℃; for 1h; Friedel-Crafts Acylation;	70%
With aluminium trichloride In 1,2-dichloro-ethane for 2h; Heating;	67%

4-methoxyphenyl-acetic chloride (4693-91-8) → O-methyl (p-methoxyphenyl)acetohydroxamate (112403-98-2)

Conditions	Yield
	99%

O-allylhydroxylamine hydrochloride (38945-21-0) + 4-methoxyphenyl-acetic chloride (4693-91-8) → N-(O-allylhydroxyl)-4-methoxyphenylacetamide (869089-90-7)

Conditions	Yield
With sodium carbonate In water; benzene at 0 - 20℃; for 12h;	99%

1,3-dibromo-2-hydroxypropane (96-21-9) + 4-methoxyphenyl-acetic chloride (4693-91-8) → 2-bromo-1-(bromomethyl)ethyl 2-(4-methoxyphenyl)acetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Inert atmosphere;	99%

N-methoxylamine hydrochloride (593-56-6) + 4-methoxyphenyl-acetic chloride (4693-91-8) → O-methyl (p-methoxyphenyl)acetohydroxamate (112403-98-2)

Conditions	Yield
With sodium carbonate In water; benzene for 5h; Ambient temperature;	98%
With sodium carbonate In water; benzene at 23℃; for 12h; Inert atmosphere; Cooling with ice;	67%
With potassium carbonate In water; ethyl acetate at 0 - 20℃;	256.5 mg

3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>-L-phenylalanine methyl ester (174905-91-0) + 4-methoxyphenyl-acetic chloride (4693-91-8) → N-<(4-methoxyphenyl)acetyl>-3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>-L-phenylalanine methyl ester (221332-90-7)

Conditions	Yield
With sodium carbonate In benzene at 8 - 10℃; for 0.5h;	98%

N-(4-cyanobenzyl)-6-aminopyrimidine-4-carboxamide hydrochloride + 4-methoxyphenyl-acetic chloride (4693-91-8) → C22H19N5O3

Conditions	Yield
With pyridine at 60℃; for 15h;	98%

(+)404-3-(4-aminophenyl)-3-ethyl-2,6-piperidinedione (55511-44-9) + 4-methoxyphenyl-acetic chloride (4693-91-8) → C22H23FN2O4 (1205648-10-7)

Conditions	Yield
Stage #1: 4-methoxyphenyl-acetic chloride With bis-triphenylphosphine-palladium(II) chloride; O-benzoylquinidine; N-fluorobis(benzenesulfon)imide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 8h; Inert atmosphere; Stage #2: (+)404-3-(4-aminophenyl)-3-ethyl-2,6-piperidinedione With dmap In tetrahydrofuran at -78 - 20℃; Inert atmosphere; optical yield given as %de;	98%

N-methylhomoveratrylamine (3490-06-0) + 4-methoxyphenyl-acetic chloride (4693-91-8) → N-(3,4-dimethoxyphenethyl)-2-(4-methoxyphenyl)-N-methylacetamide

Conditions	Yield
With sodium hydroxide In chloroform; water	98%

thiophenol (108-98-5) + 4-methoxyphenyl-acetic chloride (4693-91-8) → S-phenyl 2-(4-methoxyphenyl)ethanethioate (86211-05-4)

Conditions	Yield
With triethylamine In toluene	97%

4-methoxyphenyl-acetic chloride (4693-91-8) → 2-(4-Methoxyphenyl)ethanol (702-23-8)

Conditions	Yield
With (1,3-dimethylimidazol-2-ylidene)borane In chloroform at 20℃; for 2h;	97%

(1,3-dimethyl-1H-imidazol-3-ium-2-yl)bis(phenylthio)hydroborate + 4-methoxyphenyl-acetic chloride (4693-91-8) → S-phenyl 2-(4-methoxyphenyl)ethanethioate (86211-05-4)

Conditions	Yield
In chloroform at 20℃; for 2h;	97%

salicylaldehyde (90-02-8) + 4-methoxyphenyl-acetic chloride (4693-91-8) → 3-(4-methoxyphenyl)coumarin (23000-33-1)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In benzene for 4h; Ambient temperature;	96%
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In dichloromethane; water at 20℃;	56%

3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>-D-phenylalanine methyl ester (213692-58-1) + 4-methoxyphenyl-acetic chloride (4693-91-8) → N-<(4-methoxxyphenyl)acetyl>-3,5-dimethoxy-2-<<(4-methoxyphenyl)methyl>thio>-D-phenylalanine methyl ester (213692-59-2)

Conditions	Yield
With sodium carbonate In water; benzene at 8 - 10℃; for 0.5h;	96%
	96%

1,2-benzenedithiole (17534-15-5) + 4-methoxyphenyl-acetic chloride (4693-91-8) → 2-(4-Methoxy-benzylidene)-benzo[1,3]dithiole (62217-22-5)

Conditions	Yield
With tetrafluoroboric acid In diethyl ether at 105 - 110℃; for 0.166667h;	95%

2-(4-bromophenyl)-N-methylethan-1-amine (725683-06-7) + 4-methoxyphenyl-acetic chloride (4693-91-8) → N-(4-bromophenethyl)-2-(4-methoxyphenyl)-N-methylacetamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	95%

2-(2-bromobenzyloxy)aniline (3434-04-6) + D-Prolin (344-25-2) + 4-methoxyphenyl-acetic chloride (4693-91-8) → (R)-1-[(4-methoxyphenyl)acetyl]pyrrolidine-2-carboxylic acid

Conditions	Yield
With hydrogenchloride; sodium hydroxide In water; acetone	95%

3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (102226-41-5) + 4-methoxyphenyl-acetic chloride (4693-91-8) → 1-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-2-(4-methoxy-phenyl)-ethanone (1198154-13-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	95%

Propargylamine (2450-71-7) + 4-methoxyphenyl-acetic chloride (4693-91-8) → 2-(4-methoxyphenyl)-N-(prop-2-yn-1-yl)acetamide (1030779-93-1)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h; Huisgen Cycloaddition;	95%

pyrrolidine (123-75-1) + 4-methoxyphenyl-acetic chloride (4693-91-8) → 2-(4-methoxyphenyl)-1-(pyrrolidin-1-yl)ethan-1-one (123902-08-9)

Conditions	Yield
In dichloromethane at 20℃; for 5h; Inert atmosphere;	95%
With triethylamine In dichloromethane at 20℃;	4.18 g

1-amino-2-propene (107-11-9) + 4-methoxyphenyl-acetic chloride (4693-91-8) → N-allyl-2-(4-methoxyphenyl)acetamide

Conditions	Yield
In dichloromethane for 4h; Cooling with ice;	94%

(5-bromo-2-chloro-pyridin-3-ylmethyl)-methyl-amine (917473-39-3) + 4-methoxyphenyl-acetic chloride (4693-91-8) → N-(5-bromo-2-chloro-pyridin-3-ylmethyl)-2-(4-methoxy-phenyl)-N-methyl-acetamide (917473-40-6)

Conditions	Yield
With 4-methyl-morpholine In dichloromethane at 0 - 23℃; for 18h;	94%
With 4-methyl-morpholine In dichloromethane at 0 - 20℃; for 18.0667h;	94%

2,5-dimethoxyaniline (102-56-7) + 4-methoxyphenyl-acetic chloride (4693-91-8) → N-(2,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acetamide (256424-18-7)

Conditions	Yield
In toluene at 20℃; for 1h;	93%
In toluene; Petroleum ether	1.83 g (93%)

recorcinol (108-46-3) + 4-methoxyphenyl-acetic chloride (4693-91-8) → 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone (487-49-0)

Conditions	Yield
With hydrogen fluoride at 20℃; for 12h; Product distribution / selectivity; Friedel-Crafts acylation; autoclave;	92%
With aluminium trichloride; nitrobenzene

1,2,3-trimethoxybenzene (634-36-6) + 4-methoxyphenyl-acetic chloride (4693-91-8) → 1-(2-hydroxy-3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone (3606-32-4)

Conditions	Yield
With aluminium trichloride In carbon disulfide at 20℃;	92%
With aluminium trichloride

Upstream product

• 104-01-8 4-Methoxyphenylacetic acid 
• 79-04-9 chloroacetyl chloride 
• 156-38-7 4-hydroxyphenylacetate 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 105-13-5 4-Methoxybenzyl alcohol 
• 104-47-2 p-methoxybenzylnitrile 
• 2746-25-0 p-Methoxybenzyl bromide 

Downstream Products

• 67947-62-0 2-(4-methoxy-phenyl)-1-thiophen-2-yl-ethanone 
• 114791-70-7 (4-methoxy-phenyl)-acetic acid 2,2'-piperazine-1,4-diyl-diethyl ester 
• 20341-14-4 N-[2-(1,3-benzodioxol-5-yl)ethyl]-2-(4-methoxyphenyl)acetamide 
• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 
• 107274-12-4 4-ethoxy-4'-methoxy-deoxybenzoin 
• 51072-34-5 N-(2-cyclohex-1-enylethyl)-2-(4-methoxyphenyl)-acetamide 
• 63732-96-7 17-(4-methoxy-phenethyl)-morphinan-3-ol 
• 111036-49-8 1-(1-cyclohexenyl)-2-(4-methoxyphenyl)ethanone 
• 487-49-0 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 37167-15-0 2-[2-(4-Methoxy-phenyl)-acetyl]-cyclododecanone 
• 66164-34-9 1-(4-Methoxy-phenyl)-nonan-2-one 
• 91552-47-5 2-chloroethyl 2-(4-methoxyphenyl)acetate 
• 123331-37-3 1-<(4-Methoxyphenyl)acetyl>-4,5-dimethylimidazole 
• 135181-98-5 N-benzyl-2-(4-methoxyphenyl)-N-methylacetamide 

Relevant articles and documents

Total synthesis of two isoflavone C-glycosides (6-tert-butyl puerarin and 6-tert-butyl-4′-methoxypuerarin) through the deoxybenzoin pathway

The total synthesis of two isoflavone C-glycosides (6-tert-butylpuerarin and 6-tert-butyl-4′-methoxypuerarin) was achieved through the deoxybenzoin pathway with overall yields of 14.6% and 14.2%. The key intermediate 12 was obtained by de-tert-butylation

R - alpha - amino -4 - methoxybenzene b amide synthesis method

The invention relates to a preparing method of a compound, in particular to a compounding method of R-alpha-amino-4-anisyl phenyl acetamide, which comprises the following steps: acidylation, methylation and aminolysis. In the step of acidylation, raw mate

Diastereoselective Electrophilic Trifluoromethylthiolation of Chiral Oxazolidinones: Access to Enantiopure α-SCF3 Alcohols

Lithium imide enolates featuring Evans’ chiral oxazolidinone auxiliary were involved in diastereoselective α-trifluoromethylthiolation with electrophilic SCF3 donors. Diastereopure products were isolated and converted to enantiopure α-SCF3 alcohols without racemisation. (Figure presented.).