3,6-dichloro-4-hydroxy-2-methyl-4-<3-(2-tetrahydropyranyloxy)-1-propynyl>-2,5-cyclohexadienone

Base Information

• Chemical Name: 3,6-dichloro-4-hydroxy-2-methyl-4-<3-(2-tetrahydropyranyloxy)-1-propynyl>-2,5-cyclohexadienone
• CAS No.: 75347-64-7
• Molecular Formula: C₁₅H₁₆Cl₂O₄
• Molecular Weight: 331.196

Synonyms:3,6-dichloro-4-hydroxy-2-methyl-4-<3-(2-tetrahydropyranyloxy)-1-propynyl>-2,5-cyclohexadienone

Chemical Property of 3,6-dichloro-4-hydroxy-2-methyl-4-<3-(2-tetrahydropyranyloxy)-1-propynyl>-2,5-cyclohexadienone

Chemical Property:

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Technology Process of 3,6-dichloro-4-hydroxy-2-methyl-4-<3-(2-tetrahydropyranyloxy)-1-propynyl>-2,5-cyclohexadienone

There total 2 articles about 3,6-dichloro-4-hydroxy-2-methyl-4-<3-(2-tetrahydropyranyloxy)-1-propynyl>-2,5-cyclohexadienone 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: 36.0%

1-cyano-3,6-dichloro-2-methyl-1,4-bis<(trimethylsilyl)oxy>-4-<3-(2-tetrahydropyranyloxy)-1-propynyl>-2,5-cyclohexadiene (75347-63-6) → 3,6-dichloro-4-hydroxy-2-methyl-4-<3-(2-tetrahydropyranyloxy)-1-propynyl>-2,5-cyclohexadienone (75347-64-7)

Guidance literature:

With copper diacetate; sodium fluoride; In 1,2-dimethoxyethane; for 3h; Ambient temperature;

DOI:10.1021/jo01313a009

Reference yield:

3-(tetrahydropyran-2'-yloxy)propyne (6089-04-9) → 3,6-dichloro-4-hydroxy-2-methyl-4-<3-(2-tetrahydropyranyloxy)-1-propynyl>-2,5-cyclohexadienone (75347-64-7)

Guidance literature:

Multi-step reaction with 2 steps

2: 36 percent / sodium fluoride, cupric acetate / 1,2-dimethoxy-ethane / 3 h / Ambient temperature

With copper diacetate; sodium fluoride; In 1,2-dimethoxyethane;

DOI:10.1021/jo01313a009

Reference yield: 86.0%

3,6-dichloro-4-hydroxy-2-methyl-4-<3-(2-tetrahydropyranyloxy)-1-propynyl>-2,5-cyclohexadienone (75347-64-7) → 3,6-dichloro-4-hydroxy-2-methyl-4-<3-(2-tetrahydropyranyloxy)-1-propenyl>-2,5-cyclohexadienone (75347-65-8)

Guidance literature:

With hydrogen; Pd-BaSO₄; In pyridine; ethyl acetate; for 2h;

DOI:10.1021/jo01313a009

upstream raw materials:

1-cyano-3,6-dichloro-2-methyl-1,4-bis<(trimethylsilyl)oxy>-4-<3-(2-tetrahydropyranyloxy)-1-propynyl>-2,5-cyclohexadiene

3-(tetrahydropyran-2'-yloxy)propyne

Downstream raw materials:

3,6-dichloro-4-hydroxy-2-methyl-4-<3-(2-tetrahydropyranyloxy)-1-propenyl>-2,5-cyclohexadienone

2,5-dichloro-3-(3-hydroxy-1-propenyl)-6-methyl-1,4-benzoquinone

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