11-(benzyloxy)-3-(1-hydroxy-3-methylbut-3-en-1-yl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]-dioxocin-5-one

Base Information

Chemical Name:11-(benzyloxy)-3-(1-hydroxy-3-methylbut-3-en-1-yl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]-dioxocin-5-one
CAS No.:1374139-18-0
Molecular Formula:C₂₈H₂₈O₆
Molecular Weight:460.527
Hs Code.:

Synonyms:11-(benzyloxy)-3-(1-hydroxy-3-methylbut-3-en-1-yl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]-dioxocin-5-one

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Chemical Property of 11-(benzyloxy)-3-(1-hydroxy-3-methylbut-3-en-1-yl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]-dioxocin-5-one

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Technology Process of 11-(benzyloxy)-3-(1-hydroxy-3-methylbut-3-en-1-yl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]-dioxocin-5-one

There total 21 articles about 11-(benzyloxy)-3-(1-hydroxy-3-methylbut-3-en-1-yl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]-dioxocin-5-one 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%

: 1374139-17-9
11-(benzyloxy)-4-methoxy-9-methyl-5-oxo-5,7-dihydrodibenzo-[b,g][1,5]-dioxocine-3-carbaldehyde

: 5674-01-1
2-methylallylmagnesium chloride

: 1374139-18-0
11-(benzyloxy)-3-(1-hydroxy-3-methylbut-3-en-1-yl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]-dioxocin-5-one

Guidance literature:: In tetrahydrofuran; at -10 ℃; for 1h;
DOI:10.1002/hlca.201100405

Reference yield:

: 1374139-11-3
3-(benzyloxy)-2-{[(tert-butyl)dimethylsilyl]oxy}-5-methylbenzaldehyde

: 1374139-18-0
11-(benzyloxy)-3-(1-hydroxy-3-methylbut-3-en-1-yl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]-dioxocin-5-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium tetrahydroborate / methanol / 4 h / 0 - 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C

3.1: toluene-4-sulfonic acid / dichloromethane / 0.25 h / -20 °C

3.2: 1 h / 0 °C

4.1: dmap; copper; copper(II) oxide / acetonitrile / 12 h / Reflux

5.1: toluene-4-sulfonic acid / water; isopropyl alcohol / Reflux

6.1: toluene-4-sulfonic acid / methanol / 1 h

6.2: 12 h / Reflux

7.1: 2-chloro-1-methyl-pyridinium iodide; triethylamine / acetonitrile / 13 h / 80 °C

8.1: tetrahydrofuran / 1 h / -10 °C

With dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; copper; toluene-4-sulfonic acid; triethylamine; copper(II) oxide; In tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; acetonitrile; 4.1: Ullmann condensation;
DOI:10.1002/hlca.201100405

Reference yield:

: 2-(benzyloxy)-4-methyl-6-{[(tetrahydro-2H-pyran-2-yl)oxy]methyl}phenol

: 1374139-18-0
11-(benzyloxy)-3-(1-hydroxy-3-methylbut-3-en-1-yl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]-dioxocin-5-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: dmap; copper; copper(II) oxide / acetonitrile / 12 h / Reflux

2.1: toluene-4-sulfonic acid / water; isopropyl alcohol / Reflux

3.1: toluene-4-sulfonic acid / methanol / 1 h

3.2: 12 h / Reflux

4.1: 2-chloro-1-methyl-pyridinium iodide; triethylamine / acetonitrile / 13 h / 80 °C

5.1: tetrahydrofuran / 1 h / -10 °C

With dmap; 2-chloro-1-methyl-pyridinium iodide; copper; toluene-4-sulfonic acid; triethylamine; copper(II) oxide; In tetrahydrofuran; methanol; water; isopropyl alcohol; acetonitrile; 1.1: Ullmann condensation;
DOI:10.1002/hlca.201100405