(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-methoxycinnamic acid

Base Information

Chemical Name:(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-methoxycinnamic acid
CAS No.:1352042-70-6
Molecular Formula:C₂₆H₂₈O₄
Molecular Weight:404.506
Hs Code.:

Synonyms:(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-methoxycinnamic acid

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Chemical Property of (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-methoxycinnamic acid

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Technology Process of (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-methoxycinnamic acid

There total 5 articles about (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-methoxycinnamic 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: 70.0%

: 1352042-63-7
ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-methoxycinnamate

: 1352042-70-6
(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-methoxycinnamic acid

Guidance literature:: ethyl (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-methoxycinnamate; With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 20 ℃; for 6.3h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; methanol; water; pH=1; Inert atmosphere;
DOI:10.1021/jm2011436

Reference yield:

: 120315-65-3
4-bromo-3-methoxy-benzonitrile

: 1352042-70-6
(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-methoxycinnamic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 4.75 h / -78 - 20 °C / Inert atmosphere

1.2: 2.25 h / Inert atmosphere

2.1: toluene / 19 h / Reflux; Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane / 22.6 h / Reflux; Inert atmosphere

4.1: boron tribromide / dichloromethane / 2 h / -78 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 6.3 h / 20 °C / Inert atmosphere

5.2: pH 1 / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium hydroxide monohydrate; boron tribromide; diisobutylaluminium hydride; sodium carbonate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; toluene; 2.1: Wittig reaction / 3.1: Suzuki-Miyaura coupling;
DOI:10.1021/jm2011436

Reference yield:

: 1352042-54-6
(E)-ethyl 3-(4-bromo-3-methoxyphenyl)acrylate

: 1352042-70-6
(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-methoxycinnamic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane / 22.6 h / Reflux; Inert atmosphere

2.1: boron tribromide / dichloromethane / 2 h / -78 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 6.3 h / 20 °C / Inert atmosphere

3.2: pH 1 / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium hydroxide monohydrate; boron tribromide; sodium carbonate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; 1.1: Suzuki-Miyaura coupling;
DOI:10.1021/jm2011436