Cyclohexanecarboxylic acid, 3-hydroxy-, methyl ester, (1R,3S)-

Base Information

• Chemical Name: Cyclohexanecarboxylic acid, 3-hydroxy-, methyl ester, (1R,3S)-
• CAS No.: 70144-91-1
• Molecular Formula: C8H14O3
• Molecular Weight: 158.197
• Mol file: 70144-91-1.mol

Synonyms:(+/-)-methyl (1S*,3R*)-3-hydroxycyclohexanecarboxylate;racemic methyl cis-3-hydroxycyclohexane-1-carboxylate;cis-3-Hydroxy-cyclohexancarbonsaeure-methylester;cis-3-hydroxy-cyclohexanecarboxylic acid methyl ester;(-)-cis-3-Hydroxycyclohexancarbonsaeuremethylester;methyl cis-3-hydroxycyclohexanecarboxylate;

Chemical Property of Cyclohexanecarboxylic acid, 3-hydroxy-, methyl ester, (1R,3S)-

Chemical Property:

• PSA: 46.53000
• LogP: 0.71050

Purity/Quality:

≥98% ^*data from raw suppliers

(1R,3S)-Methyl3-hydroxycyclohexanecarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclohexanecarboxylic acid, 3-hydroxy-, methyl ester, (1R,3S)-

There total 27 articles about Cyclohexanecarboxylic acid, 3-hydroxy-, methyl ester, (1R,3S)- 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%

methanol (67-56-1) + sodium methylate (124-41-4) + 6-oxabicyclo[3.2.1]octan-7-one (4350-83-8) → (+/-)-methyl cis-3-hydroxycyclohexanecarboxylate (6125-56-0,6183-54-6,37722-82-0,49543-00-2,70144-91-1,99438-46-7,99438-47-8,99438-48-9,149055-86-7)

Guidance literature:

methanol; sodium methylate; 6-oxabicyclo[3.2.1]octan-7-one; at 20 ℃; for 18h; pH=12;

With acetic acid; In methanol; pH=6;

Reference yield: 63.3%

methanol (67-56-1) + 4-bromo-6-oxabicyclo[3.2.1]octan-7-one → methyl (1R,3S)-3-hydroxycyclohexane-1-carboxylate (70144-91-1)

Guidance literature:

With palladium on activated charcoal; hydrogen; sodium carbonate; at 55 ℃; for 16h; under 15001.5 Torr; Autoclave;

Reference yield:

(1R,5R)-methyl-5-hydroxycyclohex-3-enecarboxylate (54911-89-6,68295-80-7,74561-99-2,79433-96-8,121053-59-6,121053-60-9,126640-65-1,68295-79-4) → methyl (1R,3S)-3-hydroxycyclohexane-1-carboxylate (70144-91-1)

Guidance literature:

With hydrogen; 5% Rh/Al2O3; In tetrahydrofuran; for 24h; under 1034.32 Torr;

upstream raw materials:

3-oxo-cyclohexanecarboxylic acid methyl ester

(1R)-methyl 3-oxocyclohexanecarboxylate

(1R,5R)-methyl-5-hydroxycyclohex-3-enecarboxylate

(RS)-3-oxocyclohexanecarbonitrile

Downstream raw materials:

C₂₂H₃₂O₁₂

Refernces

• 1、 -. "GLYCOMIMETIC INHIBITORS OF SIGLEC-8". Page/Page column 12; 1/3. . Retrieved 2008/06/13.
• 2、 -. "METHOD FOR THE PREPARATION OF ENANTIOMER FORMS OF CIS-CONFIGURED 3-HYDROXYCYCLOHEXANE CARBOXYLIC ACID DERIVATIVES USING HYDROLASES". Page/Page column 21. . Retrieved 2008/06/13.