4-Hydroxy-3,5-dimethyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-dienone

Base Information

• Chemical Name: 4-Hydroxy-3,5-dimethyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-dienone
• CAS No.: 182184-46-9
• Molecular Formula: C₁₆H₁₈O₃S
• Molecular Weight: 290.383

Synonyms:4-Hydroxy-3,5-dimethyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-dienone

Chemical Property of 4-Hydroxy-3,5-dimethyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-dienone

Chemical Property:

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Technology Process of 4-Hydroxy-3,5-dimethyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-dienone

There total 2 articles about 4-Hydroxy-3,5-dimethyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-dienone 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:

4,4-Dimethoxy-2,6-dimethyl-1-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-dienol (1027594-94-0) → 4-Hydroxy-3,5-dimethyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-dienone (182184-46-9)

Guidance literature:

With oxalic acid; In tetrahydrofuran; water; Yield given;

DOI:10.1021/jo9712308

Reference yield:

(R)-methyl p-tolyl sulfoxide (1519-39-7) → 4-Hydroxy-3,5-dimethyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-dienone (182184-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1: BuLi, diisopropylamine / hexane; tetrahydrofuran / 2 h / -78 °C

2: 5percent oxalic acid / tetrahydrofuran; H₂O

With n-butyllithium; oxalic acid; diisopropylamine; In tetrahydrofuran; hexane; water;

DOI:10.1021/jo9712308

Reference yield: 87.0%

1-hexyn-1-yl-dimethylaluminum (66530-04-9) + 4-Hydroxy-3,5-dimethyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-dienone (182184-46-9) → (4R,5R)-5-Hex-1-ynyl-4-hydroxy-3,5-dimethyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohex-2-enone

Guidance literature:

In dichloromethane; at 0 ℃; for 3h;

DOI:10.1021/jo961126a

upstream raw materials:

4,4-Dimethoxy-2,6-dimethyl-1-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-dienol

(R)-methyl p-tolyl sulfoxide

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