Cyclohexaneacetic acid, a-ethenyl-1-hydroxy-

Base Information

• Chemical Name: Cyclohexaneacetic acid, a-ethenyl-1-hydroxy-
• CAS No.: 41955-33-3
• Molecular Formula: C10H16O3
• Molecular Weight: 184.235
• Mol file: 41955-33-3.mol

Synonyms:

Chemical Property of Cyclohexaneacetic acid, a-ethenyl-1-hydroxy-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclohexaneacetic acid, a-ethenyl-1-hydroxy-

There total 4 articles about Cyclohexaneacetic acid, a-ethenyl-1-hydroxy- 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%

4-bromocrotonic acid (13991-36-1) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 2-(1-hydroxycyclohexyl)but-3-enoic acid (41955-33-3)

Guidance literature:

4-bromocrotonic acid; With indium; In methanol;

cyclohexanone; In methanol; at 50 ℃; for 16h;

DOI:10.1071/CH03212

Reference yield: 70.0%

3-butenoictrimethylsilylester (13688-54-5) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 2-(1-hydroxycyclohexyl)but-3-enoic acid (41955-33-3)

Guidance literature:

3-butenoictrimethylsilylester; With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃; for 0.5h;

cyclohexanone; In tetrahydrofuran; hexane; at -70 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; hexane; at -70 - 20 ℃; Further stages.;

DOI:10.1021/jo020128u

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + acide γ-bromocrotonique + allyl bromide (106-95-6) → γ-(1-Hydroxy-1-cyclohexyl)-crotonsaeure (7465-10-3) + 2-(1-hydroxycyclohexyl)but-3-enoic acid (41955-33-3)

Guidance literature:

With zinc; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, 0 deg C; 2.) THF, reflux, 4 h;

DOI:10.1016/S0040-4020(01)96531-7

upstream raw materials:

(E)-but-2-enoic acid

cyclohexanone

allyl bromide

3-butenoictrimethylsilylester

Downstream raw materials:

2-(1-hydroxy-cyclohexyl)-but-3-enoic acid methyl ester

Refernces

• 1、 Bowyer, Michael C.,Gordon, Charles M.,Leitch, Sarah K.,McCluskey, Adam,Ritchie, Craig. "Indium-mediated addition of 4-bromocrotonic acid to aldehydes and ketones-A simple, high yielding route to αallyl-β-hydroxy carboxylic acids". . p. 135 - 137. Retrieved 2007/10/03.
• 2、 Bellassoued, M.,Habbachi, F.,Gaudemar, M.. "SUR LA REACTION DE PREFORMATSKY. PREPARATION ET REACTIVITE DE L'ORGANOZINCIQUE ISSU DU SEL BROMOZINCIQUE DE L'ACIDE γ-BROMOCROTONIQUE". . p. 1299 - 1306. Retrieved 2007/10/02.