(1S,2R)-2-Formyl-cyclohexanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2R)-2-Formyl-cyclohexanecarboxylic acid methyl ester
• CAS No.: 149564-35-2
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.208
• Mol file: 149564-35-2.mol

Synonyms:(1S,2R)-2-Formyl-cyclohexanecarboxylic acid methyl ester

Chemical Property of (1S,2R)-2-Formyl-cyclohexanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-2-Formyl-cyclohexanecarboxylic acid methyl ester

There total 8 articles about (1S,2R)-2-Formyl-cyclohexanecarboxylic acid methyl ester 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: 71.0%

methyl trans-2-(hydroxymethyl)cyclohexane-1-carboxylate → methyl trans-2-formylcyclohexane-1-carboxylate (64109-98-4,105074-19-9,149564-35-2)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.2174/1570178614666171130161203

Reference yield:

(1S-cis)-6-Chlorcarbonyl-3-cyclohexen-1-carbonsaeure-methylester (19914-76-2,35033-75-1,91179-09-8,93531-06-7,104265-86-3,104265-87-4,104265-89-6) → (1S,2R)-2-Formyl-cyclohexanecarboxylic acid methyl ester (149564-35-2)

Guidance literature:

With 2,6-dimethylpyridine; hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 25 ℃; under 2068.6 Torr; Yield given;

DOI:10.1016/S0040-4039(00)77633-7

Reference yield:

cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5) → (1S,2R)-2-Formyl-cyclohexanecarboxylic acid methyl ester (149564-35-2)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / 23 °C

2: oxalyl chloride / toluene / 18 h / 23 °C

3: hydrogen, 2,6-lutidine / 5 percent Pd/C / tetrahydrofuran / 25 °C / 2068.6 Torr

With 2,6-dimethylpyridine; oxalyl dichloride; hydrogen; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4039(00)77633-7

upstream raw materials:

methanol

8,8-dichlorobicyclo[4.2.0]octan-7-one

cyclohexene

1,2-cis-cyclohexanedicarboxylic anhydride

Downstream raw materials:

(1R,2R)-2-(3-Acetylsulfanyl-2-methyl-propionyl)-cyclohexanecarboxylic acid benzhydryl ester

diphenylmethyl trans-2-(1-oxo-2-methyl-2-propenyl)cyclohexanecarboxylate

(1R,2R)-2-(1-Hydroxy-2-methyl-allyl)-cyclohexanecarboxylic acid benzhydryl ester

trans-2-<3-(acetylthio)-2-methyl-1-oxopropyl>cyclohexanecarboxylic acid