3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic acid methyl ester

Base Information

Chemical Name:3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic acid methyl ester
CAS No.:134209-07-7
Molecular Formula:C₁₉H₂₀O₅
Molecular Weight:328.365
Hs Code.:

Synonyms:3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic acid methyl ester

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Chemical Property of 3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic acid methyl ester

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Technology Process of 3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic acid methyl ester

There total 3 articles about 3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic 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:

: 134209-03-3
3-[3-(4-Formyl-phenoxy)-4-hydroxy-phenyl]-propionic acid methyl ester

: 134209-07-7
3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / potassium bis(trimethylsilyl)amide (KHMDS), 18-crown-6 / tetrahydrofuran / 0.5 h / -60 °C

2: 91 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 50 °C

3: 1.) Et(iPr)2N, Cl₃CCH₂OCOCl, 2.) NaBH₄ / 1.) THF, 0 deg C, 45 min, 2.) THF-DMF, 0 deg C, 15 min

With sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; 2,2,2-Trichloroethyl chloroformate; In tetrahydrofuran;
DOI:10.1021/jo00013a024

Reference yield:

: 134209-05-5
(Z)-3-{4-[2-Hydroxy-5-(2-methoxycarbonyl-ethyl)-phenoxy]-phenyl}-acrylic acid 2-trimethylsilanyl-ethyl ester

: 134209-07-7
3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 50 °C

2: 1.) Et(iPr)2N, Cl₃CCH₂OCOCl, 2.) NaBH₄ / 1.) THF, 0 deg C, 45 min, 2.) THF-DMF, 0 deg C, 15 min

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; 2,2,2-Trichloroethyl chloroformate; In tetrahydrofuran;
DOI:10.1021/jo00013a024

Reference yield:

: 134209-06-6
(Z)-3-{4-[2-Hydroxy-5-(2-methoxycarbonyl-ethyl)-phenoxy]-phenyl}-acrylic acid

: 134209-07-7
3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; N-ethyl-N,N-diisopropylamine; 2,2,2-Trichloroethyl chloroformate; Yield given. Multistep reaction; 1.) THF, 0 deg C, 45 min, 2.) THF-DMF, 0 deg C, 15 min;
DOI:10.1021/jo00013a024