3562-99-0

Basic information

• Product Name: 3-(4-METHOXY-1-NAPHTHOYL)PROPIONIC ACID
• Synonyms: 3-(4-METHOXY-1-NAPHTHOYL)PROPIONIC ACID;3-(4-methoxy-1-naphthoyl)-propionicaci;4-methoxy-gamma-oxo-1-naphthalenebutanoicaci;acidebeta-(1-methoxy-4-naphthoyl)propionique;beta-(1-methoxy-4-naphthoyl)-propionsaeure;epanaftol;fel-bis;genabil
• CAS NO: 3562-99-0
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27
• EINECS: 222-631-2
• Product Categories: Aromatic Propionic Acids
• Mol File: 3562-99-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 172-173°
• Boiling Point: 361.52°C (rough estimate)
• Flash Point: 196.6 °C
• Appearance: COA
• Density: 1.2105 (rough estimate)
• Vapor Pressure: 3.04E-09mmHg at 25°C
• Refractive Index: 1.4872 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.44±0.17(Predicted)
• CAS DataBase Reference: 3-(4-METHOXY-1-NAPHTHOYL)PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-METHOXY-1-NAPHTHOYL)PROPIONIC ACID(3562-99-0)
• EPA Substance Registry System: 3-(4-METHOXY-1-NAPHTHOYL)PROPIONIC ACID(3562-99-0)

Safety Data

• Hazardous Substances Data: 3562-99-0(Hazardous Substances Data)

Usage

Uses

Menbutone is a cholerectic compound which is used for stimulating gastro-intestinal function by promoting secretory processes in animals including that of cattle, sheep, goats, horses and dogs. It is used in treatment of hepatic dysfunction of dogs by promoting bile secretion.

Originator

Hepalande, Delalande ,W. Germany ,1977

Manufacturing Process

395 parts of (α-methoxynaphthalene and 265 parts of succinic anhydride are dissolved in 8,000 parts of dry benzene at room temperature. The resulting solution is stirred and 710 parts of anhydrous aluminum chloride are added over a period of twenty minutes. During the addition the temperature of the reaction mixture rises to about 60°C to 70°C. After the addition the reaction mixture is stirred for fifteen or twenty minutes at 60°C to 70°C and then refluxed for one hour. The hot reaction mixture is then poured onto a mixture of 5,000 parts of ice and 900 parts of concentrated hydrochloric acid. The benzene is removed by steam distillation and the hot aqueous residue is filtered to remove the insoluble β-(1-methoxy-4-naphthoyl)-propionic acid. The residue of the latter is dried and then dissolved in 16,000 parts of hot water containing 300 parts of sodium carbonate. The hot solution is treated with activated charcoal, filtered while hot, chilled and acidified. The residue of purified acid is collected on a filter, washed with water, and dried at 65°C. A yield of 552 parts of purified β-(1-methoxy)-4-naphthoyl)propionic acid, melting at 172°C to 173°C is obtained.

Therapeutic Function

Choleretic

InChI:InChI=1/C14H12O3/c15-13(8-9-14(16)17)12-7-3-5-10-4-1-2-6-11(10)12/h1-7H,8-9H2,(H,16,17)

Synthetic route

succinic acid anhydride (108-30-5) + 1-Methoxynaphthalene (2216-69-5) → 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 33 - 37℃; for 6h;	86.4%
With carbon disulfide; aluminium trichloride
With aluminium trichloride; nitrobenzene

4-(4-hydroxy-[1]naphthyl)-4-oxo-butyric acid (10441-51-7) + dimethyl sulfate (77-78-1) → 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0)

succinic acid anhydride (108-30-5) + carbon disulfide (75-15-0) + aluminium trichloride (7446-70-0) + 1-Methoxynaphthalene (2216-69-5) → 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0)

succinic acid anhydride (108-30-5) + aluminium trichloride (7446-70-0) + 1,1,1,2-tetrachoroethane (630-20-6) + 1-Methoxynaphthalene (2216-69-5) → 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0)

succinic acid anhydride (108-30-5) + aluminium trichloride (7446-70-0) + nitrobenzene (98-95-3) + 1-Methoxynaphthalene (2216-69-5) → 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0)

succinic acid anhydride (108-30-5) + carbon disulfide (75-15-0) + aluminium trichloride (7446-70-0) + 1-Methoxynaphthalene (2216-69-5) → 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) + 4-methoxy-naphthalene-carbodithioic acid-(1)

succinic acid anhydride (108-30-5) + 4-methoxy-naphthyl-(1)-magnesium bromide → 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0)

Conditions	Yield
With diethyl ether; benzene

α-naphthol (90-15-3) → 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3; 1,1,2,2-tetrachloro-ethane View Scheme

N1-(6-chloro-1,2,3,4-tetrahydroacridin-9-yl)butane-1,4-diamine (1040281-57-9) + 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → C32H34ClN3O3

Conditions	Yield
With 4-methyl-morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; ethyl acetate at 20℃; for 12h; Inert atmosphere;	75%

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) + N1-(6-chloro-1,2,3,4-tetrahydroacridin-9-yl)propane-1,3-diamine → C31H32ClN3O3

Conditions	Yield
With 4-methyl-morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; ethyl acetate at 20℃; for 12h; Inert atmosphere;	69%

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) + N-(1,2,3,4-tetrahydroacridin-9-yl)propane-1,3-diamine (844874-03-9) → C31H33N3O3

Conditions	Yield
With 4-methyl-morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; ethyl acetate at 20℃; for 12h; Inert atmosphere;	65%

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) + 9-(2-aminoethylamino)-1,2,3,4-tetrahydroacridine (57165-75-0) → C30H31N3O3

Conditions	Yield
With 4-methyl-morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane-d2; ethyl acetate at 20℃; for 12h; Inert atmosphere;	61%

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) + 9-(4-aminobutylamino)-1,2,3,4-tetrahydroacridine (249290-07-1) → C32H35N3O3

Conditions	Yield
With 4-methyl-morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; ethyl acetate at 20℃; for 12h; Inert atmosphere;	60%

N1-(6-chloro-1,2,3,4-tetrahydroacridin-9-yl)ethane-1,2-diamine (1392319-30-0) + 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → C30H30ClN3O3

Conditions	Yield
With 4-methyl-morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; ethyl acetate at 20℃; for 12h; Inert atmosphere;	60%

n-Pent-4-enyl alcohol (821-09-0) + 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → pent-4-en-1-yl 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;	54%

methanol (67-56-1) + 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → methyl 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoate

Conditions	Yield
With tert.-butylnitrite at 40℃; for 48h; Green chemistry;	46%

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → γ-(4-methoxy-1-naphthyl)butyric acid (10465-20-0)

Conditions	Yield
With hydrogenchloride; amalgamated zinc; acetic acid weiteres Reagens: Toluol; Behandeln des Reaktionsprodukts mit wss. Natronlauge und Dimethylsulfat;
With potassium hydroxide; hydrazine anschliessend Behandeln mit Dimethylsulfat;
With hydrogenchloride; mercury; zinc In toluene
With hydrogenchloride; zinc In toluene for 2h; Reflux;
With hydrogenchloride; zinc In water; toluene for 2h; Reflux;

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → 4-(4-hydroxy-[1]naphthyl)-4-oxo-butyric acid (10441-51-7)

Conditions	Yield
With aluminium trichloride; chlorobenzene
With sodium hydroxide

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → methyl 4-(4-methoxynaphthalen-1-yl)-4-oxobutanoate

Conditions	Yield
With diazomethane; diethyl ether
With sodium hydroxide; dimethyl sulfate

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → 4-(4-methoxy-[1]naphthyl)-4-oxo-butyric acid ethyl ester (5345-90-4)

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) + butan-1-ol (71-36-3) → 4-(4-methoxy-[1]naphthyl)-4-oxo-butyric acid butyl ester

Conditions	Yield
With toluene-4-sulfonic acid; xylene

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → 4,4'-dimethoxy-1,1'-binaphthyl (19817-09-5)

Conditions	Yield
With sodium hydroxide

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → [4R]-3-[3-Acetylthio-3-(4-methoxy-1-naphthoyl)propionyl]-4-thiazolidinecarboxylic acid

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → 1-oxo-9-methoxy-1,2,3,4-tetrahydrophenanthrene (19817-10-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: amalgamated zinc; aqueous hydrochloric acid; acetic acid / weiteres Reagens: Toluol; Behandeln des Reaktionsprodukts mit wss. Natronlauge und Dimethylsulfat 2: SOCl2; diethyl ether; pyridine / Behandeln des Reaktionsprodukts mit SnCl4 in Benzol unter Kuehlung View Scheme
Multi-step reaction with 2 steps 1: N2H4; KOH / anschliessend Behandeln mit Dimethylsulfat 2: HF View Scheme
Multi-step reaction with 2 steps 1: Zn-Hg, aq. HCl / toluene 2: polyphosphoric acid / 110 - 120 °C View Scheme

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → 10,11-dihydro-5-methoxyphenanthro<2,1-d>isoxazole (79225-67-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: N2H4; KOH / anschliessend Behandeln mit Dimethylsulfat 2: HF 3: sodium methylate; benzene 4: acetic acid; NH2OH+HCl View Scheme

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → 4-(4-hydroxy-[1]naphthyl)-butyric acid (10441-52-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: amalgamated zinc; aqueous hydrochloric acid; acetic acid / weiteres Reagens: Toluol; Behandeln des Reaktionsprodukts mit wss. Natronlauge und Dimethylsulfat 2: aqueous hydriodic acid View Scheme

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → 2-formyl-9-methoxy-1-oxo-1,2,3,4-tetrahydrophenanthrene (79225-65-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: N2H4; KOH / anschliessend Behandeln mit Dimethylsulfat 2: HF 3: sodium methylate; benzene View Scheme

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → 9-methoxy-2-methyl-1-oxo-1,2,3,4-tetrahydro-phenanthrene-2-carbonitrile

Conditions	Yield
Multi-step reaction with 5 steps 1: N2H4; KOH / anschliessend Behandeln mit Dimethylsulfat 2: HF 3: sodium methylate; benzene 4: acetic acid; NH2OH+HCl 5: sodium tert-butylate; tert-butyl alcohol View Scheme

4-(4-methoxynaphthalen-1-yl)-4-oxobutanoic acid (3562-99-0) → (9-methoxy-1-oxo-1,2,3,4-tetrahydro-[2]phenanthryl)-glyoxylic acid methyl ester (861813-68-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: amalgamated zinc; aqueous hydrochloric acid; acetic acid / weiteres Reagens: Toluol; Behandeln des Reaktionsprodukts mit wss. Natronlauge und Dimethylsulfat 2: SOCl2; diethyl ether; pyridine / Behandeln des Reaktionsprodukts mit SnCl4 in Benzol unter Kuehlung 3: sodium methylate; benzene View Scheme

Upstream product

• 108-30-5 succinic acid anhydride 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 2216-69-5 1-Methoxynaphthalene 
• 630-20-6 1,1,1,2-tetrachoroethane 
• 98-95-3 nitrobenzene 
• 90-15-3 α-naphthol 
• 10441-51-7 4-(4-hydroxy-[1]naphthyl)-4-oxo-butyric acid 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1613625-08-3 C₃₇H₄₄N₄O₅ 
• 19817-10-8 9-methoxy-1-oxo-1,2,3,4-tetrahydrophenanthrene 
• 5345-90-4 4-(4-methoxy-[1]naphthyl)-4-oxo-butyric acid ethyl ester 
• 10465-20-0 γ-(4-methoxy-1-naphthyl)butyric acid 

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