Cyclohexanecarboxylic acid, 5-ethyl-2-oxo-, methyl ester

Base Information

• Chemical Name: Cyclohexanecarboxylic acid, 5-ethyl-2-oxo-, methyl ester
• CAS No.: 114862-60-1
• Molecular Formula: C10H16O3
• Molecular Weight: 184.235
• Mol file: 114862-60-1.mol

Synonyms:

Chemical Property of Cyclohexanecarboxylic acid, 5-ethyl-2-oxo-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclohexanecarboxylic acid, 5-ethyl-2-oxo-, methyl ester

There total 2 articles about Cyclohexanecarboxylic acid, 5-ethyl-2-oxo-, 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: 93.0%

4-ethylcyclohexanone (5441-51-0) + carbonic acid dimethyl ester (616-38-6) → methyl 5-ethyl-2-oxo-cyclohexancarboxylate (114862-60-1)

Guidance literature:

With sodium hydride; In benzene; for 1.5h; Heating;

DOI:10.1021/ja001898v

Reference yield:

→ methyl 5-ethyl-2-oxo-cyclohexancarboxylate (114862-60-1)

Guidance literature:

Reference yield:

methyl 5-ethyl-2-oxo-cyclohexancarboxylate (114862-60-1) → (+)-byssochlamic acid (743-51-1)

Guidance literature:

Multi-step reaction with 15 steps

1.1: Br₂ / diethyl ether / 2.17 h / 0 °C

2.1: 39 percent / methanol / 0 - 20 °C

3.1: 98 percent / porcine liver esterase; aq. Na₂HPO₄; aq. K₂HPO₄ / acetone / 3 h / 20 °C / pH 7

4.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C

4.2: 89 percent / NaBH₄ / H₂O / 0.5 h / 0 °C

5.1: 93 percent / TsOH monohydrate / CH₂Cl₂ / 1 h / 20 °C

6.1: DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

6.2: 91 percent / Rochelle's salt / CH₂Cl₂ / 0.33 h

7.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

8.1: 71 percent / MgBr₂ / diethyl ether / 5 h / 20 °C

9.1: 60 percent / EDCl; DMAP / CH₂Cl₂ / 4 h / 20 °C

10.1: aq. HF / acetonitrile / 1.5 h / 20 °C

11.1: 23.6 mg / DCC; DMAP*HCl / CHCl₃ / 20 h / Heating

12.1: CH₂Cl₂ / Photolysis

13.1: aq. LiOH / dioxane / 1.5 h / 50 °C

14.1: KMnO₄ / H₂O; dioxane / 1 h / 40 °C

15.1: aq. HCl

With 2,6-dimethylpyridine; hydrogenchloride; porcine liver esterase; dmap; lithium hydroxide; potassium permanganate; dipotassium hydrogenphosphate; disodium hydrogenphosphate; hydrogen fluoride; bromine; 4-(dimethylamino)pyridine hydrochloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; magnesium bromide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; chloroform; water; acetone; acetonitrile; 1.1: Bromination / 2.1: Favorski rearrangement-elimination / 3.1: asymmetric hydrolysis / 4.1: Addition / 4.2: Reduction / 5.1: Addition / 6.1: Reduction / 6.2: Reduction / 7.1: silylation / 8.1: acetal cleavage / 9.1: Esterification / 10.1: desilylation / 11.1: Keck-Steglich lactonization / 12.1: Cycloaddition / 13.1: Hydrolysis / 14.1: Oxidation / 15.1: dehydrative cyclization;

DOI:10.1021/ja001898v

upstream raw materials:

4-ethylcyclohexanone

carbonic acid dimethyl ester

Downstream raw materials:

1,3-Dibromo-5-ethyl-2-oxo-cyclohexanecarboxylic acid methyl ester

(+)-byssochlamic acid

(+/-)-byssochlamic acid

8-ethyl-1-(phenylmethoxy)-7,8,9,10-tetrahydro-6H-benzonaphtho<1,2-b>pyran-6-one