5-[1,3]Dioxolan-2-yl-2,6,6-trimethyl-cyclohex-1-enecarboxylic acid methyl ester

Base Information

Chemical Name:5-[1,3]Dioxolan-2-yl-2,6,6-trimethyl-cyclohex-1-enecarboxylic acid methyl ester
CAS No.:102308-01-0
Molecular Formula:C₁₄H₂₂O₄
Molecular Weight:254.326
Hs Code.:

Synonyms:5-[1,3]Dioxolan-2-yl-2,6,6-trimethyl-cyclohex-1-enecarboxylic acid methyl ester

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Chemical Property of 5-[1,3]Dioxolan-2-yl-2,6,6-trimethyl-cyclohex-1-enecarboxylic acid methyl ester

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Technology Process of 5-[1,3]Dioxolan-2-yl-2,6,6-trimethyl-cyclohex-1-enecarboxylic acid methyl ester

There total 7 articles about 5-[1,3]Dioxolan-2-yl-2,6,6-trimethyl-cyclohex-1-enecarboxylic acid methyl ester 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:

: 40790-56-5
2,6-dimethyl-2-cyclohexen-1-one

: 102308-01-0
5-[1,3]Dioxolan-2-yl-2,6,6-trimethyl-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) CuI, 2.) HMPA / 1.) Et₂O/THF, -78 deg C, 2.5 h, 2.) -78 to 25 deg C, 16 h

2: SO₂Cl₂ / pTSA / CCl₄ / 12 h / 10 - 25 °C

3: LiCl, Li₂CO₃ / dimethylformamide / 2 h / 100 °C

4: 1.) sec-BuLi, 2.) 90percent HCOOH / 1.) THF/TMEDA, -55 to 25 deg C, 2 h, 2.) 25 deg C, 1.5 h

5: NaClO₂, NH₂SO₃H / H₂O; dioxane / 1.5 h / 0 - 25 °C

6: diethyl ether / 0.5 h / 0 °C

7: 1.) N-methyl-morpholine N-oxide, 2.) NaIO₄ / 1.) OsO₄, 3.) pTSA / 1.) acetone/H₂O, 25 deg C, 16 h (bisulfite workup), 2.) acetone/H₂O, 25 deg C, 30 min, 3.) benzene, reflux

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium periodate; copper(l) iodide; formic acid; sulfuryl dichloride; aminosulfonic acid; sec.-butyllithium; lithium carbonate; 4-methylmorpholine N-oxide; lithium chloride; osmium(VIII) oxide; toluene-4-sulfonic acid; In 1,4-dioxane; tetrachloromethane; diethyl ether; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00272a060

Reference yield:

: 102307-98-2
2,2,6-trimethyl-3-vinyl-5-cyclohexenone

: 102308-01-0
5-[1,3]Dioxolan-2-yl-2,6,6-trimethyl-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) sec-BuLi, 2.) 90percent HCOOH / 1.) THF/TMEDA, -55 to 25 deg C, 2 h, 2.) 25 deg C, 1.5 h

2: NaClO₂, NH₂SO₃H / H₂O; dioxane / 1.5 h / 0 - 25 °C

3: diethyl ether / 0.5 h / 0 °C

4: 1.) N-methyl-morpholine N-oxide, 2.) NaIO₄ / 1.) OsO₄, 3.) pTSA / 1.) acetone/H₂O, 25 deg C, 16 h (bisulfite workup), 2.) acetone/H₂O, 25 deg C, 30 min, 3.) benzene, reflux

With sodium chlorite; sodium periodate; formic acid; aminosulfonic acid; sec.-butyllithium; 4-methylmorpholine N-oxide; osmium(VIII) oxide; toluene-4-sulfonic acid; In 1,4-dioxane; diethyl ether; water;
DOI:10.1021/ja00272a060

Reference yield:

: 102307-97-1
2,2,6-Trimethyl-3-vinyl-cyclohexanone

: 102308-01-0
5-[1,3]Dioxolan-2-yl-2,6,6-trimethyl-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: SO₂Cl₂ / pTSA / CCl₄ / 12 h / 10 - 25 °C

2: LiCl, Li₂CO₃ / dimethylformamide / 2 h / 100 °C

3: 1.) sec-BuLi, 2.) 90percent HCOOH / 1.) THF/TMEDA, -55 to 25 deg C, 2 h, 2.) 25 deg C, 1.5 h

4: NaClO₂, NH₂SO₃H / H₂O; dioxane / 1.5 h / 0 - 25 °C

5: diethyl ether / 0.5 h / 0 °C

6: 1.) N-methyl-morpholine N-oxide, 2.) NaIO₄ / 1.) OsO₄, 3.) pTSA / 1.) acetone/H₂O, 25 deg C, 16 h (bisulfite workup), 2.) acetone/H₂O, 25 deg C, 30 min, 3.) benzene, reflux

With sodium chlorite; sodium periodate; formic acid; sulfuryl dichloride; aminosulfonic acid; sec.-butyllithium; lithium carbonate; 4-methylmorpholine N-oxide; lithium chloride; osmium(VIII) oxide; toluene-4-sulfonic acid; In 1,4-dioxane; tetrachloromethane; diethyl ether; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00272a060