p-Mentha-1(6),8-dien-3-ol

Base Information

• Chemical Name: p-Mentha-1(6),8-dien-3-ol
• CAS No.: 20019-62-9
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• DSSTox Substance ID: DTXSID80564630
• Nikkaji Number: J2.365.189K
• Mol file: 20019-62-9.mol

Synonyms:p-Mentha-1(6),8-dien-3-ol;20019-62-9;3-methyl-6-prop-1-en-2-ylcyclohex-3-en-1-ol;p-Mentha-1,8-dien-5-ol;p-m entha-1 ,8-dien-5-ol;SCHEMBL15013557;DTXSID80564630;CHEBI:171951;3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-en-1-ol;3-Methyl-6-(1-methylethenyl)-3-cyclohexen-1-ol, 9CI

Chemical Property of p-Mentha-1(6),8-dien-3-ol

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 191

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC(C(C1)O)C(=C)C

Technology Process of p-Mentha-1(6),8-dien-3-ol

There total 6 articles about p-Mentha-1(6),8-dien-3-ol 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: 90.0%

(+/-)-trans-p-mentha-1,8-diene-5-acetate → (+/-)-trans-p-mentha-1,8-dien-5-ol (20019-62-9,55820-19-4,58461-28-2,122620-71-7,122621-70-9)

Guidance literature:

With potassium carbonate; In methanol; for 2h;

DOI:10.1016/j.tetasy.2006.02.012

Reference yield:

(1RS,6RS)-6-acetyl-3-methylcyclohex-3-en-1-yl acetate → (+/-)-trans-p-mentha-1,8-dien-5-ol (20019-62-9,55820-19-4,58461-28-2,122620-71-7,122621-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi / tetrahydrofuran / 0.5 h / 0 °C

1.2: 78 percent / tetrahydrofuran / 3 h / 0 °C

2.1: 90 percent / K₂CO₃ / methanol / 2 h

With n-butyllithium; potassium carbonate; In tetrahydrofuran; methanol; 1.2: Wittig methylenation;

DOI:10.1016/j.tetasy.2006.02.012

Reference yield:

isoprene (78-79-5,9003-31-0) → (+/-)-trans-p-mentha-1,8-dien-5-ol (20019-62-9,55820-19-4,58461-28-2,122620-71-7,122621-70-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 43 percent / BF₃*Et₂O / CH₂Cl₂ / -40 °C

2.1: BuLi / tetrahydrofuran / 0.5 h / 0 °C

2.2: 78 percent / tetrahydrofuran / 3 h / 0 °C

3.1: 90 percent / K₂CO₃ / methanol / 2 h

With n-butyllithium; boron trifluoride diethyl etherate; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; 1.1: Diels-Alder cycloaddition / 2.2: Wittig methylenation;

DOI:10.1016/j.tetasy.2006.02.012

upstream raw materials:

trans-chrysanthenol

chrysanthenone

isoprene

Downstream raw materials:

(1S,6R)-6-(1-Chloromethyl-vinyl)-3-methyl-cyclohex-3-enol

(4S,5R)-p-mentha-1,8-diene-5-acetate

(4R,5S)-trans-p-mentha-1,8-dien-5-ol

<5R-(trans)>-p-Mentha-1,8-dien-5-ol