(1R,3R,4S)-p-menthan-3-yl hydrogen isopropylmalonate

Base Information

• Chemical Name: (1R,3R,4S)-p-menthan-3-yl hydrogen isopropylmalonate
• CAS No.: 122778-25-0
• Molecular Formula: C₁₆H₂₈O₄
• Molecular Weight: 284.396
• Mol file: 122778-25-0.mol

Synonyms:

Chemical Property of (1R,3R,4S)-p-menthan-3-yl hydrogen isopropylmalonate

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4S)-p-menthan-3-yl hydrogen isopropylmalonate

There total 2 articles about (1R,3R,4S)-p-menthan-3-yl hydrogen isopropylmalonate 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: 99.0%

C23H34O4 → (1R,3R,4S)-p-menthan-3-yl hydrogen isopropylmalonate (122778-25-0,122778-26-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; under 760.051 Torr;

DOI:10.3762/bjoc.13.5

Reference yield: 76.0%

isopropylmalonic acid (601-79-6) + (-)-menthol (2216-51-5) → (1R,3R,4S)-p-menthan-3-yl hydrogen isopropylmalonate (122778-25-0,122778-26-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile; -40 deg C, 6 h; room temperature, 10 h;

Reference yield: 87.0%

(1R,3R,4S)-p-menthan-3-yl hydrogen isopropylmalonate (122778-25-0,122778-26-1) + methyl iodide (74-88-4) → (1R,3R,4S)-p-menthan-3-yl hydrogen isopropyl(methyl)malonate (134279-48-4,134279-49-5)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 2h;

upstream raw materials:

isopropylmalonic acid

(-)-menthol

Downstream raw materials:

(S)-2-Hydroxymethyl-3-methyl-butyric acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

(1R,3R,4S)-p-menthan-3-yl (2R)-2-hydroxymethyl-3-methylbutyrate

(1R,3R,4S)-p-menthan-3-yl hydrogen isopropyl(methyl)malonate

(2S)-(+)-2,3-dimethyl-1-butanol

Refernces

• 1、 Ihara, Masataka,Takahashi, Masanobu,Taniguchi, Nobuaki,Yasui, Ken,Fukumoto, Keiichiro,Kametani, Tetsuji. "Asymmetric Syntheses of Chiral Propane-1,3-diols Starting from Malonic Acid". . p. 897 - 903. Retrieved 2007/10/02.