Menthol (-)-N,N-diethylaminoacetate

Base Information

• Chemical Name: Menthol (-)-N,N-diethylaminoacetate
• CAS No.: 81983-63-3
• Molecular Formula: C16H31NO2
• Molecular Weight: 269.428
• DSSTox Substance ID: DTXSID00231493
• Wikidata: Q76156629
• Mol file: 81983-63-3.mol

Synonyms:Menthol (-)-N,N-diethylaminoacetate;BRN 3203546;3-06-00-00164 (Beilstein Handbook Reference);81983-63-3;Glycine, N,N-diethyl-, 5-methyl-2-(1-methylethyl)cyclohexyl ester, (1R-(1-alpha,2-beta,5-alpha))-;DTXSID00231493;LS-72484

Chemical Property of Menthol (-)-N,N-diethylaminoacetate

Chemical Property:

• Vapor Pressure: 0.00016mmHg at 25°C
• Boiling Point: 331°Cat760mmHg
• Flash Point: 95.7°C
• Density: 0.94g/cm³
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 269.235479232
• Heavy Atom Count: 19
• Complexity: 274

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CC(=O)OC1CC(CCC1C(C)C)C
• Isomeric SMILES: CCN(CC)CC(=O)O[C@@H]1C[C@H](CC[C@@H]1C(C)C)C

Technology Process of Menthol (-)-N,N-diethylaminoacetate

There total 3 articles about Menthol (-)-N,N-diethylaminoacetate 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: 92.0%

(1R,2S,5R)-menthol bromoacetate (16832-20-5,32815-12-6,55284-67-8) + diethylamine (109-89-7) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(diethylamino)acetate (81983-63-3)

Guidance literature:

With sodium sulfate; sodium hydroxide; In ethyl acetate; for 6h; Solvent;

Reference yield:

(-)-menthol (2216-51-5) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(diethylamino)acetate (81983-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1: concentrated sulfuric acid

With sulfuric acid;

Reference yield:

2-isopropyl-5-methylcyclohexyl chloroethanoate (106916-72-7) + diethylamine (109-89-7) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(diethylamino)acetate (81983-63-3)

Guidance literature:

upstream raw materials:

2-isopropyl-5-methylcyclohexyl chloroethanoate

diethylamine

(-)-menthol

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

Downstream raw materials:

trans-1-methyl-3-(N,N-diethylamino)-4-phenyl-2-azetidinone