(-)-Menthyl chloride

Base Information

• Chemical Name: (-)-Menthyl chloride
• CAS No.: 29707-60-6
• Molecular Formula: C10H19 Cl
• Molecular Weight: 174.714
• European Community (EC) Number: 240-200-7
• NSC Number: 55430
• Nikkaji Number: J129.476H
• Mol file: 29707-60-6.mol

Synonyms:16052-42-9;(-)-Menthyl chloride;(1s,2r,4r)-2-chloro-1-isopropyl-4-methylcyclohexane;(-)-3-Chloro-p-menthane;Cyclohexane, 2-chloro-4-methyl-1-(1-methylethyl)-, (1S,2R,4R)-;(1S,2R,4R)-2-chloro-4-methyl-1-propan-2-ylcyclohexane;C10H19Cl;(1S,2R,4R)-2-chloro-4-methyl-1-(propan-2-yl)cyclohexane;NSC55430;(1R,2S,5R)-(-)-Menthyl chloride;(--)menthyl chloride;(?)-Menthyl chloride;(-)-Menthyl chloride, 98%;SCHEMBL10001723;Cyclohexane, 2-chloro-4-methyl-1-(1-methylethyl)-, (1S-(1alpha,2beta,4beta))-;MFCD00001481;NSC-55430;AS-71351;BB 0260390;CS-0328614;M0834;T71870;Cyclohexane, [1S-(1.alpha.,2.beta.,4.beta.)]-;J-009730;(1R)-(-)-Menthyl chloride, (1S,2R,4R)-2-Chloro-1-isopropyl-1-methylcyclohexane, [1S-(1alpha,2beta,4beta)]-2-Chloro-4-methyl-1-(methylethyl)cyclohexane

Chemical Property of (-)-Menthyl chloride

Chemical Property:

• Boiling Point: 216.1°Cat760mmHg
• Flash Point: 78.9°C
• PSA: 0.00000
• Density: 0.92g/cm³
• LogP: 3.68600
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 174.1175283
• Heavy Atom Count: 11
• Complexity: 120

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)Cl)C(C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)Cl)C(C)C

Technology Process of (-)-Menthyl chloride

There total 6 articles about (-)-Menthyl chloride 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: 96.0%

(1S,2R,5S)-(+)-menthol (15356-60-2) → (+)-(1S,2S,5R)-menthyl chloride (13371-12-5,16052-42-9,26348-39-0,28953-96-0,29707-60-6,80483-49-4,80483-50-7,104012-59-1,65494-15-7)

Guidance literature:

With Me₂SeCl₂; triphenylphosphine; In benzene; for 24h; Ambient temperature;

DOI:10.1021/jo981324x

Reference yield: 83.0%

(-)-menthol (2216-51-5) → (+)-(1S,2S,5R)-menthyl chloride (13371-12-5,16052-42-9,26348-39-0,28953-96-0,29707-60-6,80483-49-4,80483-50-7,104012-59-1,65494-15-7)

Guidance literature:

With triphenylphosphine; In tetrachloromethane; toluene; for 0.5h; Reflux; Inert atmosphere;

DOI:10.1039/c2ob07074j

Reference yield:

3-chloro-3-(3-neomenthyloxy)diazirine → 3-p-menthene (500-00-5) + (+/-)-(3R,6S)-3-isopropyl-6-methyl-1-cyclohexene (1124-26-1) + 1-chloro-2-isopropyl-5-methylcyclohexane + 1-chloro-2-isopropyl-5-methylcyclohexane (29707-60-6)

Guidance literature:

In 1,2-dichloro-ethane; at 25 ℃; Further Variations:; Reagents; Solvents; Product distribution; Photolysis;

DOI:10.1021/jo030100y

upstream raw materials:

(1S,2R,5S)-(+)-menthol

(-)-menthol

l-(-)-(Menthyloxy)triphenylphosphonium triflate

Downstream raw materials:

1-Menthyl cation

2-[1-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyl)-meth-(E)-ylidene]-pentanal

2-[1-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyl)-meth-(E)-ylidene]-butyraldehyde

(E)-3-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-2-methyl-propenal

Refernces

• 1、 Moss, Robert A.,Johnson, Lauren A.,Kacprzynski, Monica,Sauers, Ronald R.. "Fragmentation of menthyl- and neomenthyloxychlorocarbenes: Elimination and substitution reactions of alicyclic oxychlorocarbenes". . p. 5114 - 5118. Retrieved 2007/10/03.
• 2、 Dean, Christopher,Whittaker, David. "Reactions of Cyclohexane Derivatives in Superacids". . p. 1541 - 1543. Retrieved 2007/10/02.