1-(2,2-dimethyl-propionyloxymethyl)-3-methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester

Base Information

• Chemical Name: 1-(2,2-dimethyl-propionyloxymethyl)-3-methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester
• CAS No.: 913602-79-6
• Molecular Formula: C₁₆H₂₄O₅
• Molecular Weight: 296.364
• Mol file: 913602-79-6.mol

Synonyms:1-(2,2-dimethyl-propionyloxymethyl)-3-methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester

Chemical Property of 1-(2,2-dimethyl-propionyloxymethyl)-3-methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2,2-dimethyl-propionyloxymethyl)-3-methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester

There total 3 articles about 1-(2,2-dimethyl-propionyloxymethyl)-3-methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic 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: 66.0%

methyl 5-methoxy-3-((tert-butyldimethylsilyl)oxymethyl)benzoate (1126431-84-2) + iodomethyl pivaloate (53064-79-2) → 1-(2,2-dimethyl-propionyloxymethyl)-3-methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester (913602-79-6) + C22H38O6Si (1410799-74-4)

Guidance literature:

methyl 5-methoxy-3-((tert-butyldimethylsilyl)oxymethyl)benzoate; With ammonia; lithium; tert-butyl alcohol; In tetrahydrofuran; at -65 - 15 ℃; for 0.5h; Inert atmosphere;

iodomethyl pivaloate; With ammonium chloride; In tetrahydrofuran; at -65 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo301872n

Reference yield:

iodomethyl pivaloate (53064-79-2) + methyl 3-methoxy-5-methylbenzoate (108593-44-8) → 1-(2,2-dimethyl-propionyloxymethyl)-3-methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester (913602-79-6)

Guidance literature:

methyl 3-methoxy-5-methylbenzoate; With lithium; tert-butyl alcohol; In tetrahydrofuran; ammonia; at -78 ℃; for 1h;

iodomethyl pivaloate; In tetrahydrofuran; ammonia; for 2h;

DOI:10.1021/ol061802n

Reference yield:

Chloromethyl pivalate (18997-19-8) → 1-(2,2-dimethyl-propionyloxymethyl)-3-methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester (913602-79-6) + C22H38O6Si (1410799-74-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium iodide / 16 h / 20 °C / Inert atmosphere

2.1: ammonia; lithium; tert-butyl alcohol / tetrahydrofuran / 0.5 h / -65 - 15 °C / Inert atmosphere

2.2: 0.5 h / -65 °C / Inert atmosphere

With ammonia; lithium; sodium iodide; tert-butyl alcohol; In tetrahydrofuran; 2.1: |Birch Reduction / 2.2: |Birch Reduction;

DOI:10.1021/jo301872n

upstream raw materials:

iodomethyl pivaloate

methyl 3-methoxy-5-methylbenzoate

methyl 5-methoxy-3-((tert-butyldimethylsilyl)oxymethyl)benzoate

Chloromethyl pivalate

Downstream raw materials:

3-methoxy-5-methyl-2,5-cyclohexadiene-1,1-dimethanol