(E)-8-[2-Formyl-4-(4-methoxy-benzyloxy)-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-8-[2-Formyl-4-(4-methoxy-benzyloxy)-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester
• CAS No.: 543724-59-0
• Molecular Formula: C₂₅H₃₂O₅
• Molecular Weight: 412.526
• Mol file: 543724-59-0.mol

Synonyms:(E)-8-[2-Formyl-4-(4-methoxy-benzyloxy)-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester

Chemical Property of (E)-8-[2-Formyl-4-(4-methoxy-benzyloxy)-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-8-[2-Formyl-4-(4-methoxy-benzyloxy)-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester

There total 15 articles about (E)-8-[2-Formyl-4-(4-methoxy-benzyloxy)-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic 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: 92.0%

(E)-8-[2-[1,3]Dioxolan-2-yl-4-(4-methoxy-benzyloxy)-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester (543724-58-9) → (E)-8-[2-Formyl-4-(4-methoxy-benzyloxy)-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester (543724-59-0)

Guidance literature:

With water; pyridinium p-toluenesulfonate; In acetone; for 3h; Heating;

DOI:10.1139/v02-196

Reference yield:

4,4-ethylenedioxycyclohexan-1-ol (22428-87-1) → (E)-8-[2-Formyl-4-(4-methoxy-benzyloxy)-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester (543724-59-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: KH / tetrahydrofuran / 1 h / 0 °C

1.2: 96 percent / tetrahydrofuran / 0 - 20 °C

2.1: 92 percent / PPTS; H₂O / acetone / 5.5 h / Heating

3.1: PhS(O)OMe; KH / tetrahydrofuran / 0.5 h / 20 °C

3.2: 82 percent / Na₂CO₃ / toluene / 0.5 h / Heating

4.1: Br₂ / CCl₄ / 1.75 h / 0 °C

5.1: 9.58 g / Et₃N / CCl₄ / 0.67 h

6.1: n-BuLi / tetrahydrofuran / 2.5 h / 0 °C

6.2: CeCl₃ / tetrahydrofuran / 5 h / -78 °C

7.1: 10.01 g / tetrahydrofuran / -78 - 20 °C

8.1: t-BuLi / diethyl ether / -78 - 0 °C

8.2: CuCN / diethyl ether; tetrahydrofuran / 1 h / -68 °C

8.3: 92 percent / diethyl ether; tetrahydrofuran / 3 h / -50 - 0 °C

9.1: n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

9.2: 90 percent / tetrahydrofuran / 1 h / -78 °C

10.1: PPTS / benzene / 6 h / Heating

11.1: 3.66 g / TBAF / tetrahydrofuran / 6 h / 20 °C

12.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

13.1: NaH / tetrahydrofuran / 1.25 h / 0 °C

13.2: 2.72 g / tetrahydrofuran / 0.5 h / 0 °C

14.1: 92 percent / PPTS; H₂O / acetone / 3 h / Heating

With n-butyllithium; methyl benzenesulfinate; tetrabutyl ammonium fluoride; water; bromine; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; acetone; benzene;

DOI:10.1139/v02-196

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → (E)-8-[2-Formyl-4-(4-methoxy-benzyloxy)-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester (543724-59-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: NaBH₄ / methanol / 3 h / 0 °C

2.1: KH / tetrahydrofuran / 1 h / 0 °C

2.2: 96 percent / tetrahydrofuran / 0 - 20 °C

3.1: 92 percent / PPTS; H₂O / acetone / 5.5 h / Heating

4.1: PhS(O)OMe; KH / tetrahydrofuran / 0.5 h / 20 °C

4.2: 82 percent / Na₂CO₃ / toluene / 0.5 h / Heating

5.1: Br₂ / CCl₄ / 1.75 h / 0 °C

6.1: 9.58 g / Et₃N / CCl₄ / 0.67 h

7.1: n-BuLi / tetrahydrofuran / 2.5 h / 0 °C

7.2: CeCl₃ / tetrahydrofuran / 5 h / -78 °C

8.1: 10.01 g / tetrahydrofuran / -78 - 20 °C

9.1: t-BuLi / diethyl ether / -78 - 0 °C

9.2: CuCN / diethyl ether; tetrahydrofuran / 1 h / -68 °C

9.3: 92 percent / diethyl ether; tetrahydrofuran / 3 h / -50 - 0 °C

10.1: n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

10.2: 90 percent / tetrahydrofuran / 1 h / -78 °C

11.1: PPTS / benzene / 6 h / Heating

12.1: 3.66 g / TBAF / tetrahydrofuran / 6 h / 20 °C

13.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

14.1: NaH / tetrahydrofuran / 1.25 h / 0 °C

14.2: 2.72 g / tetrahydrofuran / 0.5 h / 0 °C

15.1: 92 percent / PPTS; H₂O / acetone / 3 h / Heating

With sodium tetrahydroborate; n-butyllithium; methyl benzenesulfinate; tetrabutyl ammonium fluoride; water; bromine; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; acetone; benzene;

DOI:10.1139/v02-196

upstream raw materials:

(E)-8-[2-[1,3]Dioxolan-2-yl-4-(4-methoxy-benzyloxy)-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester

4,4-ethylenedioxycyclohexan-1-ol

cyclohexanedione monoethylene ketal

4-(4-methoxy-benzyloxy)-cyclohex-2-enone

Downstream raw materials:

(E)-8-[2-Formyl-4-hydroxy-cyclohex-2-en-(E)-ylidene]-4-methyl-oct-2-enoic acid methyl ester