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

Base Information

Chemical Name:3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic acid
CAS No.:134209-08-8
Molecular Formula:C₁₈H₁₈O₅
Molecular Weight:314.338
Hs Code.:

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

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

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

There total 4 articles about 3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic 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: 82.0%

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

: 134209-08-8
3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; water; at 25 ℃; for 5h;
DOI:10.1021/jo00013a024

Reference yield:

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

: 134209-08-8
3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic acid

Guidance literature:: Multi-step reaction with 4 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

4: 82 percent / LiOH / tetrahydrofuran; methanol; H₂O / 5 h / 25 °C

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

Reference yield:

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

: 134209-08-8
3-{4-Hydroxy-3-[4-((Z)-3-hydroxy-propenyl)-phenoxy]-phenyl}-propionic acid

Guidance literature:: Multi-step reaction with 2 steps

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

2: 82 percent / LiOH / tetrahydrofuran; methanol; H₂O / 5 h / 25 °C

With lithium hydroxide; sodium tetrahydroborate; N-ethyl-N,N-diisopropylamine; 2,2,2-Trichloroethyl chloroformate; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo00013a024