4-(6,7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-4-yl)phenol

Base Information

• Chemical Name: 4-(6,7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-4-yl)phenol
• CAS No.: 1616781-25-9
• Molecular Formula: C₁₈H₂₁NO₃
• Molecular Weight: 299.37

Synonyms:4-(6,7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-4-yl)phenol

Chemical Property of 4-(6,7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-4-yl)phenol

Chemical Property:

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Technology Process of 4-(6,7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-4-yl)phenol

There total 11 articles about 4-(6,7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-4-yl)phenol 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: 60.0%

[2-(3,4-dimethoxyphenyl)-2-phenoxyethyl]methylamine (1616788-87-4) → 4-(6,7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-4-yl)phenol (1616781-25-9)

Guidance literature:

With boron trifluoride diethyl etherate; In ethyl acetate; at 0 - 20 ℃; for 2.25h;

DOI:10.1080/00397911.2014.891745

Reference yield:

C12H18NO3(1-)*K(1+) → 4-(6,7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-4-yl)phenol (1616781-25-9)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 - 120 °C

2: sodium hydrogencarbonate / toluene / 2.5 h / 120 °C

3: sodium hydroxide / dimethyl sulfoxide / 6 h / 125 °C

4: formaldehyd / acetic acid / 1 h / 90 °C / Inert atmosphere

5: boron trifluoride diethyl etherate / ethyl acetate / 2.25 h / 0 - 20 °C

With formaldehyd; boron trifluoride diethyl etherate; sodium hydrogencarbonate; potassium hydroxide; sodium hydroxide; In acetic acid; dimethyl sulfoxide; ethyl acetate; toluene; 4: |Pictet-Spengler Synthesis;

DOI:10.1080/00397911.2014.891745

Reference yield:

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → 4-(6,7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-4-yl)phenol (1616781-25-9)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium hydroxide / dimethyl sulfoxide / 0.75 h / 85 °C

2: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 - 120 °C

3: sodium hydrogencarbonate / toluene / 2.5 h / 120 °C

4: sodium hydroxide / dimethyl sulfoxide / 6 h / 125 °C

5: formaldehyd / acetic acid / 1 h / 90 °C / Inert atmosphere

6: boron trifluoride diethyl etherate / ethyl acetate / 2.25 h / 0 - 20 °C

With formaldehyd; boron trifluoride diethyl etherate; sodium hydrogencarbonate; potassium hydroxide; sodium hydroxide; In acetic acid; dimethyl sulfoxide; ethyl acetate; toluene; 5: |Pictet-Spengler Synthesis;

DOI:10.1080/00397911.2014.891745

upstream raw materials:

1-(3,4-dimethoxyphenyl)-2-(dimethylamino)ethanone

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol

[2-(3, 4-dimethoxyphenyl)-2-phenoxyethyl]dimethylamine

[2-(3, 4-dimethoxyphenyl)-2-phenoxyethyl]methylcarbamic acid ethyl ester

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