trans-4-Hydroxy-alpha,alpha,4-trimethylcyclohex-2-ene-1-methanol

Base Information

• Chemical Name: trans-4-Hydroxy-alpha,alpha,4-trimethylcyclohex-2-ene-1-methanol
• CAS No.: 54164-91-9
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.252
• European Community (EC) Number: 259-006-9,259-007-4
• DSSTox Substance ID: DTXSID30202510
• Nikkaji Number: J269.478F
• Wikidata: Q83075799
• Mol file: 54164-91-9.mol

Synonyms:EINECS 259-006-9;54164-90-8;trans-4-Hydroxy-alpha,alpha,4-trimethylcyclohex-2-ene-1-methanol;54164-91-9;cis-4-Hydroxy-alpha,alpha,4-trimethylcyclohex-2-ene-1-methanol;2-Cyclohexene-1-methanol, 4-hydroxy-alpha,alpha,4-trimethyl-, (1R,4R)-;SCHEMBL1039305;trans-p-Menth-2-en-1,8-diol;DTXSID30202510;p-Menth-2-en-1,8-diol, trans;XWFVRMWMBYDDFY-WPRPVWTQSA-N;(1R)-4alpha-Hydroxy-alpha,alpha,4-trimethyl-2-cyclohexene-1beta-methanol;2-Cyclohexene-1-methanol, 4-hydroxy-.alpha.,.alpha.,4-trimethyl-, cis-;2-Cyclohexene-1-methanol, 4-hydroxy-.alpha.,.alpha.,4-trimethyl-, trans-

Chemical Property of trans-4-Hydroxy-alpha,alpha,4-trimethylcyclohex-2-ene-1-methanol

Chemical Property:

• Boiling Point: 268°Cat760mmHg
• Flash Point: 122°C
• Density: 1.048g/cm³
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 170.130679813
• Heavy Atom Count: 12
• Complexity: 196

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CCC(C=C1)C(C)(C)O)O
• Isomeric SMILES: C[C@]1(CC[C@H](C=C1)C(C)(C)O)O

Technology Process of trans-4-Hydroxy-alpha,alpha,4-trimethylcyclohex-2-ene-1-methanol

There total 5 articles about trans-4-Hydroxy-alpha,alpha,4-trimethylcyclohex-2-ene-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:

1α-hydroxy-2β-phenylseleno-trans-p-menthan-8-ol (76338-34-6,76338-38-0) → trans-p-menth-2-ene-1,8-diol (15910-72-2,20053-40-1,54164-90-8,54164-91-9,57030-53-2)

Guidance literature:

With pyridine; dihydrogen peroxide; Yield given. Multistep reaction; 1.) tetrahydrofuran, 2.) reflux;

DOI:10.1039/P19810000756

Reference yield:

terpineol (98-55-5,2438-12-2) → trans-p-menth-2-ene-1,8-diol (15910-72-2,20053-40-1,54164-90-8,54164-91-9,57030-53-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) m-chloroperbenzoic acid

2: 1) 30percent H₂O₂ / 2) heating

With dihydrogen peroxide; 3-chloro-benzenecarboperoxoic acid;

DOI:10.1039/c39800000762

Reference yield:

1,2-epoxy-8-hydroxy-p-menthane (54145-81-2,54164-87-3,57761-51-0,57761-52-1,88494-86-4,91547-99-8,71242-69-8) → trans-p-menth-2-ene-1,8-diol (15910-72-2,20053-40-1,54164-90-8,54164-91-9,57030-53-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaBH₄ / 1.) EtOH, 2.) room temperature

2: 1.) 30percent H₂O₂, 2.) pyridine / 1.) tetrahydrofuran, 2.) reflux

With pyridine; sodium tetrahydroborate; dihydrogen peroxide;

DOI:10.1039/P19810000756

upstream raw materials:

1α-hydroxy-2β-phenylseleno-trans-p-menthan-8-ol

terpineol

1,2-epoxy-8-hydroxy-p-menthane

Downstream raw materials:

6-(1-hydroxy-1-methylethyl)-3-methyl-2-cyclohexen-1-one

1,8-diacetoxy-trans-p-menth-2-ene

Refernces

• 1、 Kametani, Tetsuji,Kurobe, Hiroshi,Nemoto, Hideo. "Studies on the stereochemical course of selenium-assisted cyclisation: Biogenetic-type synthesis in the p-menthan series". . p. 762 - 763. Retrieved 2007/10/02.