1-METHYL-3-CYCLOHEXENE-1-METHANOL

Base Information

• Chemical Name: 1-METHYL-3-CYCLOHEXENE-1-METHANOL
• CAS No.: 50552-10-8
• Molecular Formula: C8H14O
• Molecular Weight: 126.199
• Hs Code.: 2906199090
• NSC Number: 97520
• Mol file: 50552-10-8.mol

Synonyms:1-Methyl-3-cyclohexene-1-methanol;1-Methyl-3-cyclohexenemethanol;NSC 97520;

Chemical Property of 1-METHYL-3-CYCLOHEXENE-1-METHANOL

Chemical Property:

• Vapor Pressure: 0.416mmHg at 25°C
• Refractive Index: 1.469
• Boiling Point: 172.6 °C at 760 mmHg
• Flash Point: 66.4 °C
• PSA: 20.23000
• Density: 0.922 g/cm³
• LogP: 1.72510
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 126.104465066
• Heavy Atom Count: 9
• Complexity: 118

Purity/Quality:

98%min ^*data from raw suppliers

1-METHYL-3-CYCLOHEXENE-1-METHANOL Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC=CC1)CO

Technology Process of 1-METHYL-3-CYCLOHEXENE-1-METHANOL

There total 5 articles about 1-METHYL-3-CYCLOHEXENE-1-METHANOL 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: 89.0%

methyl 1-methyl-3-cyclohexenecarboxylate (6493-80-7,357418-50-9) → 1-Hydroxymethyl-1-methyl-cyclohex-3-en (50552-10-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1055/s-2008-1078569

Reference yield:

(1S)-4,7,7-trimethyl-2-azabicyclo<2.2.1>heptan-3-one (24326-88-3,183505-74-0) → ((R)-1-Methyl-cyclohex-3-enyl)-methanol (50552-10-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / tetrahydrofuran / 0 °C

2: MeAlCl₂ / CH₂Cl₂ / -30 °C

3: LAH

With lithium aluminium tetrahydride; methylaluminum dichloride; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00032a051

Reference yield:

(1R,4S)-3-Methacryloyl-1,7,7-trimethyl-3-azabicyclo<2.2.1>heptan-2-one (139278-33-4) → ((R)-1-Methyl-cyclohex-3-enyl)-methanol (50552-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: MeAlCl₂ / CH₂Cl₂ / -30 °C

2: LAH

With lithium aluminium tetrahydride; methylaluminum dichloride; In dichloromethane;

DOI:10.1021/ja00032a051

upstream raw materials:

methyl 1-methyl-3-cyclohexenecarboxylate

(1S,4R)-4,7,7-Trimethyl-2-((R)-1-methyl-cyclohex-3-enecarbonyl)-2-aza-bicyclo[2.2.1]heptan-3-one

(1S)-4,7,7-trimethyl-2-azabicyclo<2.2.1>heptan-3-one

(1R,4S)-3-Methacryloyl-1,7,7-trimethyl-3-azabicyclo<2.2.1>heptan-2-one

Downstream raw materials:

4-Methyl-4-nitrosooxymethyl-cyclohexene

1-methyl-3-cyclohexene-1-carboxaldehyde

C₁₆H₂₂O₂

Refernces

• 1、 Boeckman, Robert K.,Nelson, Scott G.,Gaul, Michael D.. "Toward the Development of a General Chiral Auxiliary. 1. Preparation of a New Class of Camphor Lactam Imides and Their Application to the Construction of Quaternary Centers via Diels-Alder Cycloaddition". . p. 2258 - 2260. Retrieved 2007/10/02.