6397-82-6

Basic information

• Product Name: 4'-methoxyhexanophenone
• Synonyms: 4'-methoxyhexanophenone;1-(4-Methoxyphenyl)-1-hexanone;1-Methoxy-4-hexanoylbenzene;4-Methoxyphenylpentyl ketone;Einecs 229-010-5;1-(4-METHOXYPHENYL)HEXAN-1-ONE(WXG01688);1-(4-METHOXYPHENYL)HEXAN-1-ONE
• CAS NO: 6397-82-6
• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.28082
• EINECS: 229-010-5
• Mol File: 6397-82-6.mol
• Article Data: 64

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4'-methoxyhexanophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-methoxyhexanophenone(6397-82-6)
• EPA Substance Registry System: 4'-methoxyhexanophenone(6397-82-6)

Safety Data

• Hazardous Substances Data: 6397-82-6(Hazardous Substances Data)

Usage

General Description

4'-methoxyhexanophenone is a chemical compound with the molecular formula C13H18O2. It is a highly flammable and hazardous substance, commonly used in the production of designer drugs and as a precursor in the synthesis of pharmaceuticals. This chemical is classified as a ketone and is known for its distinctive fruity and sweet odor. It is important to handle 4'-methoxyhexanophenone with caution, as it can cause irritation to the skin, eyes, and respiratory system upon contact or inhalation. Additionally, this compound has the potential to react violently with oxidizing agents, posing a fire hazard. Due to the potential risks associated with 4'-methoxyhexanophenone, it is essential to use proper safety precautions and handle it in a controlled environment.

Synthetic route

n-hexanoic anhydride (2051-49-2) + methoxybenzene (100-66-3) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With trifluorormethanesulfonic acid; titanium(IV) chloride tris(trifluoromethanesulfonate) In acetonitrile for 12h; Product distribution; Ambient temperature; other anhydrides and ethers; var. additives; var. solvents;	98%
With trifluorormethanesulfonic acid; titanium(IV) chloride tris(trifluoromethanesulfonate) In acetonitrile for 12h; Ambient temperature;	98%
With antimonypentachloride; lithium perchlorate In dichloromethane for 0.5h; Heating;	94%

2-(4-methoxy-phenyl)-2-pentyl-[1,3]dithiane (769936-21-2) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In methanol at 20℃; for 4.5h;	97%

1-(p-methoxyphenyl)-t-2-methylcyclopentan-r-1-ol (101934-23-0) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With 2,3,5-trimethyl-pyridine; [Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)2(5,5'-bis(trifluoromethyl)-2,2'-bipyridyl)](PF6); thiophenol In dichloromethane at 20℃; Sealed tube; Inert atmosphere; Irradiation;	97%

methoxybenzene (100-66-3) + hexanoic acid (142-62-1) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With hydrothermally synthesized Nb2O5-WOx nanofiber crystal calcined in N2 at 139.84℃; for 3h; Friedel Crafts acylation; Inert atmosphere;	93%
With tetrachlorosilane; 4-(trifluoromethyl)benzoic anhydride; silver perchlorate In dichloromethane for 24h; Ambient temperature;	89%
With tetrachlorosilane; 4-(trifluoromethyl)benzoic anhydride; silver perchlorate In dichloromethane for 76h; Ambient temperature;	84%

Hexanoyl chloride (142-61-0) + methoxybenzene (100-66-3) → 4'-methoxyhexanophenone (6397-82-6) + 1-(2-methoxyphenyl)-hexan-1-one (35031-70-0) + 1-(3-methoxyphenyl)-hexan-1-one (342423-70-5)

Conditions	Yield
With rhenium(I) pentacarbonyl bromide In 1,2-dichloro-ethane for 2h; Heating;	A 92% B n/a C n/a
With rhenium(I) pentacarbonyl bromide In 1,2-dichloro-ethane for 2h; Heating;	A n/a B 92% C n/a
With rhenium(I) pentacarbonyl bromide In 1,2-dichloro-ethane for 2h; Heating;	A n/a B n/a C 92%

n-hexanoic anhydride (2051-49-2) + 4-methoxyphenylboronic acid (5720-07-0) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With palladium diacetate; P(p-CH3OC6H4)3 at 60℃; for 16h;	91%
With sodium dodecyl-sulfate; potassium carbonate; palladium dichloride In water at 60℃; for 6h;	30%

n-hexanoic anhydride (2051-49-2) + 4-methoxyphenylboronic acid (5720-07-0) → 4'-methoxyhexanophenone (6397-82-6) + hexanoic acid (142-62-1)

Conditions	Yield
With P(p-CH3OC6H4)3; palladium diacetate In tetrahydrofuran; water at 60℃; for 16h;	A 91% B n/a

2-Hydroxy-1,2-bis-(4-methoxy-phenyl)-heptan-1-one (73172-46-0) → 4'-methoxyhexanophenone (6397-82-6) + 4-methoxybenzoic acid (100-09-4)

Conditions	Yield
With potassium hydroxide; dihydrogen peroxide	A 90% B n/a

4-(hexyn-1-yl)anisole (131558-77-5) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With water; toluene-4-sulfonic acid In ethanol for 60h; Reflux; regioselective reaction;	90%
With toluene-4-sulfonic acid In ethanol at 120℃; for 0.5h; microwave irradiation;	85%
With toluene-4-sulfonic acid In ethanol at 78℃; for 60h;	81%

1-bromo-4-methoxy-benzene (104-92-7) + hexanal (66-25-1) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With pyrrolidine; 1,3-bis-(diphenylphosphino)propane; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 115℃; for 6h; Heck reaction; Molecular sieve;	90%

1-(4-methoxyphenyl)ethanone (100-06-1) + butan-1-ol (71-36-3) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With potassium phosphate tribasic trihydrate; 5%-palladium/activated carbon In water at 180℃; for 1.5h; Microwave irradiation;	89%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine; potassium hydroxide at 100℃; for 6h; Inert atmosphere; Sealed tube;	89%
With trifuran-2-yl-phosphane; C48H34F6N4O4Pd2; lithium hydroxide In neat (no solvent) at 100℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;	85%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium hydroxide at 110℃; for 0.166667h; Aldol Condensation; Inert atmosphere;	81%
With potassium hydroxide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine at 100℃; for 4h;

1-(4-methoxyphenyl)cyclohexanol (17138-79-3) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With 2,3,5-trimethyl-pyridine; [Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)2(5,5'-bis(trifluoromethyl)-2,2'-bipyridyl)](PF6); thiophenol In dichloromethane at 20℃; for 12h; Reagent/catalyst; Sealed tube; Inert atmosphere; Irradiation;	89%
With tetrabutylphosphonium dimethyl phosphate; 2,4,6-Triisopropylthiophenol; [Ir(2-(2,4-difluorophenyl)-4-(trifluoromethyl)pyridine)2(5,5'-bis(trifluoromethyl)-2,2'-bipyridine)]PF6 In toluene at 20℃; for 24h; Glovebox; Sealed tube; Irradiation;	82%

trimethylsilyl hexanoate (14246-15-2) + methoxybenzene (100-66-3) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With tetrachlorosilane; 4-(trifluoromethyl)benzoic anhydride; silver perchlorate In dichloromethane for 76h; Ambient temperature;	84%
With tetrachlorosilane; 4-(trifluoromethyl)benzoic anhydride; silver perchlorate In dichloromethane for 76h; Ambient temperature;	84%

C13H19N3O → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
Stage #1: C13H19N3O With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 4h; Inert atmosphere; Stage #2: With water In dimethyl sulfoxide; mineral oil for 0.25h; Inert atmosphere;	83%

1-penten (109-67-1) + 4-Methoxybenzyl alcohol (105-13-5) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With 2-Amino-4-methylpyridine; rhodium(III) chloride; triphenylphosphine at 130℃; for 12h;	77%

4-methoxyphenylboronic acid (5720-07-0) + hexanal (66-25-1) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With potassium phosphate; platinacycle; pentan-3-one In toluene at 90 - 100℃;	75%

4-methoxyphenyl triflate (66107-29-7) + hexanal (66-25-1) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With Quinuclidine; bis(1,5-cyclooctadiene)nickel (0); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 110℃; for 20h; Inert atmosphere; Sealed tube;	72%

p-methylbenzoic anhydride (13222-85-0) + methoxybenzene (100-66-3) → 4'-methoxyhexanophenone (6397-82-6) + 4-methoxy-4'-methylbenzophenone (23886-71-7)

Conditions	Yield
With tetrachlorosilane; silver perchlorate; hexanoic acid In dichloromethane for 24h; Ambient temperature;	A 71% B 2%

rac-1-(4-methoxyphenyl)-ethanol (3319-15-1) + butan-1-ol (71-36-3) → 4'-methoxyhexanophenone (6397-82-6) + 1-(4-methoxylphenyl)-1-hexanol (129145-41-1, 71434-60-1)

Conditions	Yield
With sodium hydroxide; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In toluene at 110℃; for 17h;	A 22% B 69%

4-chloromethoxybenzene (623-12-1) + hexanal (66-25-1) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With pyrrolidine; 2-(di-tert-butylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl acetamide at 140℃; for 4h; Inert atmosphere; Molecular sieve;	67%

Isopropenyl acetate (108-22-5) + 1-(4-methoxylphenyl)-1-hexanol (129145-41-1, 71434-60-1) → 4'-methoxyhexanophenone (6397-82-6) + C15H22O3 (129145-43-3)

Conditions	Yield
With dicarbonyl(chloro)(η5-pentaphenylcyclopentadienyl)ruthenium(II); potassium tert-butylate; sodium carbonate In di-isopropyl ether at 30℃; for 72h; Inert atmosphere; Molecular sieve; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;	A 16% B 67%

1-penten (109-67-1) + 4-methoxy-benzaldehyde (123-11-5) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With 3-methylpyridin-2-ylamine; Wilkinson's catalyst In toluene at 150℃; for 24h;	66%

1-bromo-4-methoxy-benzene (104-92-7) + (E)-1-(hex-1-en-1-yl)pyrrolidine (99175-55-0) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With pyrrolidine; 1,3-bis-(diphenylphosphino)propane; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 115℃; for 6h; Inert atmosphere; Molecular sieve;	65%

methoxybenzene (100-66-3) + 2-methylbenzoic anhydride (607-86-3) → (4-methoxyphenyl)(2-methylphenyl)methanone (41204-59-5) + 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With tetrachlorosilane; silver perchlorate; hexanoic acid In dichloromethane for 24h; Ambient temperature;	A 11% B 64%

Hexanoyl chloride (142-61-0) + methoxybenzene (100-66-3) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With aluminium trichloride In dichloromethane at 0℃; for 2h;	63%
With o-tetrachloroquinone; (η5,η5-(C5H4)2SiMe2)Mo2(CO)6 In 1,2-dichloro-ethane at 80℃; for 24h; Reagent/catalyst; Friedel-Crafts Acylation; Inert atmosphere; Schlenk technique;	42.2%
With molybdenum

methoxybenzene (100-66-3) + p-Methoxybenzoic anhydride (794-94-5) → bis(p-methoxyphenyl)methanone (90-96-0) + 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With tetrachlorosilane; silver perchlorate; hexanoic acid In dichloromethane for 24h; Ambient temperature;	A 7% B 60%

1-bromo-4-methoxy-benzene (104-92-7) + Hexanoyl chloride (142-61-0) → 4'-methoxyhexanophenone (6397-82-6) + 4,4'-(hex-1-ene-1,1-diyl)bis(methoxybenzene)

Conditions	Yield
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane Flow reactor; Stage #2: Hexanoyl chloride In tetrahydrofuran; hexane; dichloromethane Flow reactor;	A 55% B 16%

2-methoxybenzoic anhydride (64508-50-5) + methoxybenzene (100-66-3) → 4'-methoxyhexanophenone (6397-82-6) + 2,4'-dimethoxybenzophenone (5449-69-4)

Conditions	Yield
With tetrachlorosilane; silver perchlorate; hexanoic acid In dichloromethane for 24h; Ambient temperature;	A 43% B 24%

(E)-1-(hex-1-en-1-yl)pyrrolidine (99175-55-0) + 4-chloromethoxybenzene (623-12-1) → 4'-methoxyhexanophenone (6397-82-6)

Conditions	Yield
With pyrrolidine; 2-(di-tert-butylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl acetamide at 140℃; for 4h; Inert atmosphere; Molecular sieve;	41%

4'-methoxyhexanophenone (6397-82-6) → (R)-1-(4-methoxylphenyl)-1-hexanol (71434-60-1, 129145-41-1)

Conditions	Yield
With borane; Oxazaborolidine 1 In tetrahydrofuran at -10℃; for 0.2h;	99%
With sodium isopropylate; isopropyl alcohol; [RuCl2(PPh3)(ip-FOXAP)] at 20℃; for 2h;

4'-methoxyhexanophenone (6397-82-6) → (S)-1-(4-methoxylphenyl)-1-hexanol

Conditions	Yield
With hydrogen In tetrahydrofuran at 20℃; under 7500.75 Torr; for 16h;	94%

methanol (67-56-1) + 4'-methoxyhexanophenone (6397-82-6) → (±)1-(4-methoxyphenyl)-2-methylhexan-1-one (17180-57-3)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; oxygen; triphenylphosphine; potassium hydroxide at 65℃; for 48h; Inert atmosphere; Sealed tube;	94%
With C50H32F12N4O4Pd2; lithium tert-butoxide; tricyclohexylphosphine at 120℃; for 48h; Inert atmosphere; Schlenk technique;	86%

4'-methoxyhexanophenone (6397-82-6) → (E)‐1‐(4‐methoxyphenyl)hex‐2‐en‐1‐one

Conditions	Yield
With N-tert-butyl benzenesulfinimidoyl chloride; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h;	93%

4'-methoxyhexanophenone (6397-82-6) → 2-bromo-1-(4'-methoxyphenyl)-hexan-1-one (33809-55-1)

Conditions	Yield
With bromine; aluminium trichloride In diethyl ether	90%
With bromine; acetic acid In diethyl ether at 20℃;	89%
With aluminum (III) chloride; bromine In dichloromethane at 0℃; for 2h;

dimethyl L-tartrate (608-68-4) + 4'-methoxyhexanophenone (6397-82-6) → Dimethyl (4R,5R)-2-(4-methoxyphenyl)-2-pentyl-1,3-dioxolane-4,5-dicarboxylate

Conditions	Yield
With methanesulfonic acid; trimethyl orthoformate at 95℃; for 120h; Condensation; Cyclization;	69%

4'-methoxyhexanophenone (6397-82-6) + p-nitrophenyl p-methoxybenzoate (7464-46-2) → 2-n-butyl-1,3-bis(4-methoxyphenyl)propane-1,3-dione (322399-91-7)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 1.5h;	69%

Upstream product

• 142-61-0 Hexanoyl chloride 
• 100-66-3 methoxybenzene 
• 2051-49-2 n-hexanoic anhydride 
• 142-62-1 hexanoic acid 
• 541-88-8 Chloroacetic anhydride 
• 16644-66-9 1,1,1-tribromo-pentane 
• 123-11-5 4-methoxy-benzaldehyde 
• 2589-72-2 1-(4-hydroxy-phenyl)-hexan-1-one 
• 77-78-1 dimethyl sulfate 
• 73172-46-0 2-Hydroxy-1,2-bis-(4-methoxy-phenyl)-heptan-1-one 
• 13222-85-0 p-methylbenzoic anhydride 
• 14246-15-2 trimethylsilyl hexanoate 
• 64508-50-5 2-methoxybenzoic anhydride 
• 794-94-5 p-Methoxybenzoic anhydride 

Downstream Products

• 81693-80-3 1-hexyl-4-methoxybenzene 
• 17404-01-2 4-<1-Pentylhepten-(1)-yl>-anisol 
• 17403-98-4 4-(1-Pentylhex-1-enyl)-anisol 
• 120553-88-0 (Z)-3-(4-methoxyphenyl)-2-octenal 
• 71434-60-1 (R)-1-(4-methoxylphenyl)-1-hexanol 
• 120556-12-9 (R,S)-3-hydroxy-3-(4-methoxyphenyl)octanenitrile 
• 322399-91-7 2-n-butyl-1,3-bis(4-methoxyphenyl)propane-1,3-dione 
• 33809-55-1 2-bromo-1-(4'-methoxyphenyl)-hexan-1-one 
• 612824-86-9 2-azido-1-(4'-methoxyphenyl)-hexan-1-one 
• 612824-89-2 2,5-bis-n-butyl-3,6-bis-(4'-methoxyphenyl)-pyrazine 
• 381229-22-7 2-butyl-1,3,4-tris(4-methoxyphenyl)butane-1,4-dione 
• 381229-34-1 3-butyl-2,4,5-tris(4-methoxyphenyl)furan 
• 322399-93-9 4-butyl-3,5-bis(4-methoxyphenyl)-1-phenyl-1H-pyrazole 
• 322399-95-1 4-butyl-1,3,5-tris(4-methoxyphenyl)-1H-pyrazole 

Relevant articles and documents

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Friedel-Crafts (F-C) acylation of anisole with octanoic acid was carried out on tungsten oxide (WO3) supported on various types of oxide supports. We have found that the highest activity was obtained when TiO2 was used as the support. WO3/TiO2 was found to be active in the acylation of anisole with carboxylic acids of varying alkyl chain lengths (C6–C10). It was possible to recycle the WO3/TiO2 catalyst for up to 5 times without deactivation. The turnover frequency (TOF) of the catalyst was closely correlated with the electronegativity of the cation of the support used for WO3. When a strong basic oxide such as CeO2 was used as a support, the acid strength of WO3 was diminished, while the strong acidity of WO3 was retained on a weak basic support like TiO2. This explains why the acid strength and consequently, the activity, were found to be the highest for the WO3/TiO2 catalyst. The trend of the catalytic performance was consistent with the order of acid strength of WO3 on different supports measured by temperature-programmed desorption of NH3.