6-Isopropyl-7-methoxy-1-tetralone

Base Information

• Chemical Name: 6-Isopropyl-7-methoxy-1-tetralone
• CAS No.: 22009-41-2
• Molecular Formula: C14H18 O2
• Molecular Weight: 218.296
• Hs Code.: 2914509090
• DSSTox Substance ID: DTXSID00435676
• Nikkaji Number: J979.372K
• Wikidata: Q82250735
• Mol file: 22009-41-2.mol

Synonyms:6-isopropyl-7-methoxy-1-tetralone;22009-41-2;7-methoxy-6-(propan-2-yl)-1,2,3,4-tetrahydronaphthalen-1-one;7-methoxy-6-propan-2-yl-3,4-dihydro-2H-naphthalen-1-one;SCHEMBL8811980;DTXSID00435676;HHDVEHBPKKQPPQ-UHFFFAOYSA-N;7-methoxy-6-isopropyltetral-1-one;6-Isopropyl-7-methoxytetralin-1-one;MFCD09263489;AKOS016384243;NS-02573

Chemical Property of 6-Isopropyl-7-methoxy-1-tetralone

Chemical Property:

• PSA: 26.30000
• LogP: 3.33760
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 218.130679813
• Heavy Atom Count: 16
• Complexity: 260

Purity/Quality:

99% ^*data from raw suppliers

6-Isopropyl-7-methoxy-1-tetralone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(C=C2C(=C1)CCCC2=O)OC

Technology Process of 6-Isopropyl-7-methoxy-1-tetralone

There total 9 articles about 6-Isopropyl-7-methoxy-1-tetralone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

7-Methoxy-1-tetralone (6836-19-7) + isopropyl alcohol (67-63-0,8013-70-5) → 6-isopropyl-7-methoxy-3,4-dihydronaphthalen-1(2H)-one (22009-41-2)

Guidance literature:

With polyphosphoric acid; at 75 - 80 ℃; for 5h; Reflux;

DOI:10.1080/00304948.2014.903146

Reference yield: 81.0%

4-(3'-Isopropyl-4'-methoxyphenyl)butyric acid (39863-61-1) → 6-isopropyl-7-methoxy-3,4-dihydronaphthalen-1(2H)-one (22009-41-2)

Guidance literature:

With phosphoric acid; phosphorus pentoxide; In dichloromethane; at 70 - 80 ℃; for 0.333333h;

DOI:10.1021/jo00298a029

Reference yield:

o-isopropylanisole (2944-47-0) → 6-isopropyl-7-methoxy-3,4-dihydronaphthalen-1(2H)-one (22009-41-2)

Guidance literature:

Multi-step reaction with 5 steps

1: AlCl₃ / CH₂Cl₂ / 6 h / Ambient temperature

2: 5 N NaOH / ethanol / 3 h / Ambient temperature

3: KOH, hydrazine monohydrate, diethylene glycol / 6 h / 140 °C

4: thionyl chloride / benzene / 0.67 h / Heating

5: AlCl₃ / CS₂ / 4 h / Heating

With potassium hydroxide; sodium hydroxide; aluminium trichloride; thionyl chloride; hydrazine hydrate; diethylene glycol; In carbon disulfide; ethanol; dichloromethane; benzene;

DOI:10.1021/jm00016a020

upstream raw materials:

4-(3'-Isopropyl-4'-methoxyphenyl)butyric acid

4-(3-Isopropyl-4-methoxy-phenyl)-butyryl chloride

o-isopropylanisole

4-Oxo-4-(3'-isopropyl-4'-methoxyphenyl)butyric acid

Downstream raw materials:

1-phenyl-1,2,3,4-tetrahydro-6-isopropyl-7-methoxynapht-1-ol

1,2,3,4-tetrahydro-7-isopropylnaphthalene-5,6-dione

2-isopropyl-5-phenylnaphth-3-ol

3-isopropyl-8-phenylnaphthalene-1,2-dione

Refernces

• 1、 Cabrera, Elvia V.,Gil, Ariana C.,Ortega, Jose G.,Bedoya, Liadis,Sanchez, Jennifer,Banerjee, Ajoy K.. "A one-pot synthesis of 6-isopropyl-7-methoxy-1-tetralone and 6-isopropyl-7-methoxy-2-tetralone". . p. 272 - 276. Retrieved 2014.
• 2、 Yoshimura,Nagai,Hibi,Kikuchi,Abe,Hida,Higashi,Yamanaka. "A novel type of retinoic acid receptor antagonist: Synthesis and structure-activity relationships of heterocyclic ring-containing benzoic acid derivatives". . p. 3163 - 3173. Retrieved 2007/10/02.