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

Base Information

Chemical Name:(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-carboxycinnamic acid
CAS No.:1352042-69-3
Molecular Formula:C₂₆H₂₆O₅
Molecular Weight:418.489
Hs Code.:

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

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

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

There total 8 articles about (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-carboxycinnamic 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: 71.0%

: 1352042-68-2
(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-(methoxycarbonyl)cinnamic acid

: 1352042-69-3
(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-carboxycinnamic acid

Guidance literature:: (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-(methoxycarbonyl)cinnamic acid; With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; for 21h; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; methanol; water; at 82 ℃; for 24h; Inert atmosphere;

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

Reference yield:

: 1352042-51-3
ethyl (E)-4-benzyloxy-3-carbomethoxycinnamate

: 1352042-69-3
(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-carboxycinnamic acid

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: Inert atmosphere

2.1: pyridine / dichloromethane / 23 h / 0 - 20 °C / Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium chloride / 1,2-dimethoxyethane / 22 h / Reflux; Inert atmosphere

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

4.2: Inert atmosphere

5.1: sodium hydroxide / methanol; water / 1.5 h / Reflux; Inert atmosphere

5.2: Inert atmosphere

6.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 21 h / Inert atmosphere

6.2: 24 h / 82 °C / Inert atmosphere

6.3: Inert atmosphere

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

Reference yield:

: 860000-78-8
methyl 2-(benzyloxy)-5-bromobenzoate

: 1352042-69-3
(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-carboxycinnamic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: palladium diacetate; tris-(o-tolyl)phosphine / triethylamine / 17 h / 105 °C / Inert atmosphere

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

2.2: Inert atmosphere

3.1: pyridine / dichloromethane / 23 h / 0 - 20 °C / Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium chloride / 1,2-dimethoxyethane / 22 h / Reflux; Inert atmosphere

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

5.2: Inert atmosphere

6.1: sodium hydroxide / methanol; water / 1.5 h / Reflux; Inert atmosphere

6.2: Inert atmosphere

7.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 21 h / Inert atmosphere

7.2: 24 h / 82 °C / Inert atmosphere

7.3: Inert atmosphere

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium hydroxide monohydrate; palladium diacetate; boron tribromide; sodium carbonate; tris-(o-tolyl)phosphine; lithium chloride; sodium hydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; triethylamine; 1.1: Mizoroki-Heck reaction / 4.1: Suzuki-Miyaura coupling;
DOI:10.1021/jm2011436