3-(4-chlorophenyl)-3-butenoic acid

Base Information

• Chemical Name: 3-(4-chlorophenyl)-3-butenoic acid
• CAS No.: 81187-88-4
• Molecular Formula: C₁₀H₉ClO₂
• Molecular Weight: 196.633
• Mol file: 81187-88-4.mol

Synonyms:3-(4-chlorophenyl)-3-butenoic acid

Chemical Property of 3-(4-chlorophenyl)-3-butenoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(4-chlorophenyl)-3-butenoic acid

There total 6 articles about 3-(4-chlorophenyl)-3-butenoic acid 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: 72.0%

carbon dioxide (124-38-9,18923-20-1) + 2-(4-chlorophenyl)-3-hydroxypropene (45941-96-6) → 3-(4-chlorophenyl)-3-butenoic acid (81187-88-4)

Guidance literature:

carbon dioxide; 2-(4-chlorophenyl)-3-hydroxypropene; With diethylzinc; triphenylphosphine; palladium dichloride; In tetrahydrofuran; hexane; at 40 ℃; for 48h; under 760.051 Torr; Inert atmosphere; Sealed tube;

With hydrogenchloride; water; In tetrahydrofuran; hexane; at 0 ℃; pH=< 2; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.201503359

Reference yield: 70.0%

carbon dioxide (124-38-9,18923-20-1) + α-bromomethyl-4-chlorostyrene (89220-51-9) → 3-(4-chlorophenyl)-3-butenoic acid (81187-88-4)

Guidance literature:

carbon dioxide; α-bromomethyl-4-chlorostyrene; With indium; cesium fluoride; In N,N-dimethyl-formamide; at 60 ℃; for 14h; under 15001.5 Torr; Autoclave;

In ethyl acetate; N,N-dimethyl-formamide; regioselective reaction;

DOI:10.1039/c4cc00148f

Reference yield:

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + bromochlorobenzene (106-39-8) → 3-(4-chlorophenyl)-3-butenoic acid (81187-88-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; iodine; magnesium; zinc(II) chloride; Multistep reaction; 1.) Et₂O, 1 h, 2.) Et₂O, RT, 30 min;

DOI:10.1016/S0957-4166(98)00336-X

upstream raw materials:

ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate

4-methyleneoxetan-2-one

bromochlorobenzene

para-chloroacetophenone

Downstream raw materials:

3-(4-chlorophenyl)but-3-en-1-ol

tert-Butyl-[3-(4-chloro-phenyl)-but-3-enyloxy]-dimethyl-silane

(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(4-chloro-phenyl)-butane-1,2-diol

(R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(4-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester

Refernces

• 1、 Miao, Bukeyan,Ma, Shengming. "Direct carboxylation of allylic halides with carbon dioxide in the presence of indium". supporting information. p. 3285 - 3287. Retrieved 2014/03/21.
• 2、 Nishi, Takahide,Ishibashi, Koki,Nakajima, Katsuyoshi,Iio, Yukiko,Fukazawa, Tetsuya. "An efficient synthesis of enantiomerically pure 2-[(2R)-arylmorpholin- 2-yl]ethanols, key intermediates of tachykinin receptor antagonist". . p. 3251 - 3262. Retrieved 2007/10/03.