4-hydroxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxole-5-carbaldehyde

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Chemical Name:4-hydroxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxole-5-carbaldehyde
CAS No.:791814-44-3
Molecular Formula:C₂₁H₂₂O₆
Molecular Weight:370.402
Hs Code.:

Synonyms:4-hydroxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxole-5-carbaldehyde

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Chemical Property of 4-hydroxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxole-5-carbaldehyde

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Technology Process of 4-hydroxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxole-5-carbaldehyde

There total 9 articles about 4-hydroxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxole-5-carbaldehyde 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: 54.0%

: 791814-42-1
5-[(E)-Cyclohexyliminomethyl]-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-4-ol

: 791814-44-3
4-hydroxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxole-5-carbaldehyde

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; for 0.25h; Heating;
DOI:10.1021/jo049157q

Reference yield:

: 110-87-2
3,4-dihydro-2H-pyran

: 791814-44-3
4-hydroxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxole-5-carbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1.1: 72 percent / camphorsulfonic acid monohydrate / CH₂Cl₂ / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.2: trimethyl borate / tetrahydrofuran; hexane / 1.25 h / cooling

3.1: 77 percent / Pd(OAc)2; Ph₃P; aq. NaHCO₃ / dioxane / 12 h / Heating

4.1: toluene / 2 h / Heating

5.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / cooling

5.2: trimethylborate / tetrahydrofuran; hexane / 1.25 h / cooling

5.3: 1.70 g / hydrogen peroxide; AcOH / tetrahydrofuran; hexane / 16 h / 20 °C

6.1: 54 percent / aq. HCl / tetrahydrofuran / 0.25 h / Heating

With hydrogenchloride; palladium diacetate; n-butyllithium; camphor-10-sulfonic acid; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; toluene; 3.1: Suzuki coupling;
DOI:10.1021/jo049157q

Reference yield:

: 120-57-0,30024-74-9
piperonal

: 791814-44-3
4-hydroxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxole-5-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: 84 percent / Br₂; FeCl₃; AcOH

2.1: 77 percent / Pd(OAc)2; Ph₃P; aq. NaHCO₃ / dioxane / 12 h / Heating

3.1: toluene / 2 h / Heating

4.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / cooling

4.2: trimethylborate / tetrahydrofuran; hexane / 1.25 h / cooling

4.3: 1.70 g / hydrogen peroxide; AcOH / tetrahydrofuran; hexane / 16 h / 20 °C

5.1: 54 percent / aq. HCl / tetrahydrofuran / 0.25 h / Heating

With hydrogenchloride; palladium diacetate; n-butyllithium; bromine; iron(III) chloride; sodium hydrogencarbonate; acetic acid; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; hexane; toluene; 2.1: Suzuki coupling;
DOI:10.1021/jo049157q