1-[2-benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-phenyl]-prop-2-en-1-ol

Base Information

• Chemical Name: 1-[2-benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-phenyl]-prop-2-en-1-ol
• CAS No.: 590362-06-4
• Molecular Formula: C₂₇H₃₄O₄
• Molecular Weight: 422.565
• Mol file: 590362-06-4.mol

Synonyms:1-[2-benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-phenyl]-prop-2-en-1-ol

Chemical Property of 1-[2-benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-phenyl]-prop-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2-benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-phenyl]-prop-2-en-1-ol

There total 11 articles about 1-[2-benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-phenyl]-prop-2-en-1-ol 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: 97.0%

vinylmagnesium chloride (3536-96-7) + 2-benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-benzaldehyde (590362-00-8) → 1-[2-benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-phenyl]-prop-2-en-1-ol (590362-06-4)

Guidance literature:

In diethyl ether; at -78 - 0 ℃; for 2h;

DOI:10.1016/S0040-4039(03)01120-1

Reference yield:

3-methoxy-2-hydroxybenzaldehyde (148-53-8) → 1-[2-benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-phenyl]-prop-2-en-1-ol (590362-06-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 95 percent / Et₃N / DMAP / CH₂Cl₂ / 2 h / 20 °C

2.1: 98 percent / KBr; Br₂ / H₂O / 10 h / 22 °C

3.1: 96 percent / NaHCO₃ / methanol; H₂O / 5 h / 20 °C

4.1: 96 percent / K₂CO₃ / methanol / 5 h / 65 °C

5.1: 86 percent / NaBH₄ / methanol / 2 h / 20 °C

6.1: 98 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

7.1: tBuLi / tetrahydrofuran / 0.5 h / -78 °C

7.2: 76 percent / 2 h / -78 - 0 °C

8.1: 95 percent / NaH / tetrahydrofuran / 18 h / 20 °C

9.1: 92 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

10.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

11.1: 97 percent / diethyl ether / 2 h / -78 - 0 °C

With 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; bromine; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; triethylamine; potassium bromide; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4039(03)01120-1

Reference yield:

6-bromo-2-hydroxy-3-methoxybenzaldehyde (20035-41-0) → 1-[2-benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-phenyl]-prop-2-en-1-ol (590362-06-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 96 percent / K₂CO₃ / methanol / 5 h / 65 °C

2.1: 86 percent / NaBH₄ / methanol / 2 h / 20 °C

3.1: 98 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

4.1: tBuLi / tetrahydrofuran / 0.5 h / -78 °C

4.2: 76 percent / 2 h / -78 - 0 °C

5.1: 95 percent / NaH / tetrahydrofuran / 18 h / 20 °C

6.1: 92 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

7.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

8.1: 97 percent / diethyl ether / 2 h / -78 - 0 °C

With 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(03)01120-1

upstream raw materials:

vinylmagnesium chloride

2-benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-benzaldehyde

6-bromo-2-hydroxy-3-methoxybenzaldehyde

benzyl chloride

Downstream raw materials:

1-[2-benzyloxy-6-(3-isopropenyl-1-methoxy-4-methyl-pent-3-enyl)-3-methoxy-phenyl]-propenone