4-Cyclohexene-1,2-dicarboxylic acid, 4-acetyl-, 2-methyl ester, cis-

Base Information

• Chemical Name: 4-Cyclohexene-1,2-dicarboxylic acid, 4-acetyl-, 2-methyl ester, cis-
• CAS No.: 95375-38-5
• Molecular Formula: C₁₁H₁₄O₅
• Molecular Weight: 226.229
• Mol file: 95375-38-5.mol

Synonyms:

Chemical Property of 4-Cyclohexene-1,2-dicarboxylic acid, 4-acetyl-, 2-methyl ester, cis-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Cyclohexene-1,2-dicarboxylic acid, 4-acetyl-, 2-methyl ester, cis-

There total 1 articles about 4-Cyclohexene-1,2-dicarboxylic acid, 4-acetyl-, 2-methyl ester, cis- 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: 57.0%

1-methyl hydrogen 1,2-cis-1,2-cyclohex-4-ene dicarboxylate (93603-11-3) + acetyl chloride (75-36-5) → cis-1-carboxy-2-methoxycarbonyl-4-acetyl-4-cyclohexene (84073-89-2,95375-38-5)

Guidance literature:

With aluminium trichloride; In dichloromethane; 1) -5 deg C, 6 h; 2) RT;

DOI:10.1016/S0040-4020(01)91529-7

Reference yield:

cis-1-carboxy-2-methoxycarbonyl-4-acetyl-4-cyclohexene (84073-89-2,95375-38-5) → cis-1-carboxy-2-methoxycarbonyl-4-acetylcyclohexane (85382-54-3,95462-59-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 760 Torr; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(01)91529-7

Reference yield:

cis-1-carboxy-2-methoxycarbonyl-4-acetyl-4-cyclohexene (84073-89-2,95375-38-5) → cis-1-formyl-2-methoxycarbonyl-4-(1'-ethylendithioethyl)-cyclohexane (84073-88-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd/C / methanol / 760 Torr / Ambient temperature

2: 73 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h

3: 1) ethyl chloroformate, Et₃N; 2) NaBH₄ / 1) THF, 0 deg C, 1 h; 2) -70 deg C, 1 h

4: 74 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

With sodium tetrahydroborate; boron trifluoride diethyl etherate; hydrogen; chloroformic acid ethyl ester; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)91529-7

upstream raw materials:

1-methyl hydrogen 1,2-cis-1,2-cyclohex-4-ene dicarboxylate

acetyl chloride

Downstream raw materials:

cis-1-carboxy-2-methoxycarbonyl-4-acetylcyclohexane

4-Acetyl-2-(1,4-dimethoxy-naphthalene-2-carbonyl)-cyclohexanecarboxylic acid methyl ester

cis-1-formyl-2-methoxycarbonyl-4-(1'-ethylendithioethyl)-cyclohexane

cis-1-hydroxymethyl-2-methoxycarbonyl-4-(1'-ethylendithioethyl)-cyclohexane