3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride

Base Information

• Chemical Name: 3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride
• CAS No.: 95458-29-0
• Molecular Formula: C₂₃H₂₂O₈
• Molecular Weight: 426.423
• Mol file: 95458-29-0.mol

Synonyms:3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride

Chemical Property of 3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride

There total 11 articles about 3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride 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: 76.0%

citraconic acid anhydride (616-02-4) + 5-<1-Acetoxy-1-(3',4',5'-trimethoxyphenyl)methyl>-6-trimethylsilylmethyl-1,3-benzodioxole (1026470-10-9) → 3a,4-trans-3a,9a-cis-3a-Methyl-6,7-methylenedioxy-4-(3',4'-5'-trimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho<2,3-c>furan-1,3-dione (95106-90-4) + 3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride (95458-29-0)

Guidance literature:

With silica gel; In tetrachloromethane; at 50 ℃; for 240h; Yields of byproduct given;

DOI:10.1039/P19930001235

Reference yield:

citraconic acid anhydride (616-02-4) + 1-(3,4,5-trimethoxyphenyl)-5,6-methylenedioxy-1,3-dihydrobenzothiophene-2,2-dioxide (82792-81-2) → 8a-Methyl-5-(3,4,5-trimethoxy-phenyl)-5,5a,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-6,8-dione (95458-29-0) + 3a,4-trans-3a,9a-cis-3a-Methyl-6,7-methylenedioxy-4-(3',4'-5'-trimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho<2,3-c>furan-1,3-dione (95106-90-4)

Guidance literature:

With Phthalic acid dibutyl ester; at 160 - 200 ℃; for 3h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)83462-1

Reference yield:

piperonol (495-76-1) → 3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride (95458-29-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / 49percent aq. HBr / 2 h / Ambient temperature

2: 44.93 g / Mg / tetrahydrofuran / 0 °C

3: Br₂, Na₂CO₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

4: 1) BuLi / 1) hexane, THF, 2.5 h, -78 deg C, 2) THF, r.t., overnight

5: pyridine / 24 h / Ambient temperature

6: flash silica / CCl₄ / 240 h / 50 °C

With pyridine; n-butyllithium; hydrogen bromide; bromine; silica gel; sodium carbonate; magnesium; In tetrahydrofuran; tetrachloromethane; dichloromethane; water;

DOI:10.1039/P19930001235

upstream raw materials:

citraconic acid anhydride

1-(3,4,5-trimethoxyphenyl)-5,6-methylenedioxy-1,3-dihydrobenzothiophene-2,2-dioxide

5-<1-Acetoxy-1-(3',4',5'-trimethoxyphenyl)methyl>-6-trimethylsilylmethyl-1,3-benzodioxole

piperonol