(8S)-(-)-p-mentha-1,3-dien-9-ol

Base Information

• Chemical Name: (8S)-(-)-p-mentha-1,3-dien-9-ol
• CAS No.: 1505356-40-0
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236

Synonyms:(8S)-(-)-p-mentha-1,3-dien-9-ol

Chemical Property of (8S)-(-)-p-mentha-1,3-dien-9-ol

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (8S)-(-)-p-mentha-1,3-dien-9-ol

There total 1 articles about (8S)-(-)-p-mentha-1,3-dien-9-ol 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: 97.0%

C10H16O (1505356-38-6) → (8S)-(-)-p-mentha-1,3-dien-9-ol (1505356-40-0)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; toluene; at 0 - 20 ℃; for 3.5h; Inert atmosphere;

DOI:10.1021/ja503899t

Reference yield:

(8S)-(-)-p-mentha-1,3-dien-9-ol (1505356-40-0) + C13H18O2Si (532933-63-4) → C17H28O3Si

Guidance literature:

C₁₃H₁₈O₂Si; With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

(8S)-(-)-p-mentha-1,3-dien-9-ol; With pyridine; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ja503899t

Reference yield:

(8S)-(-)-p-mentha-1,3-dien-9-ol (1505356-40-0) → C44H59NO5Si2

Guidance literature:

Multi-step reaction with 23 steps

1.1: trifluorormethanesulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: diethylaluminium chloride / hexane; toluene / 39 h / 0 - 20 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / diethyl ether / 1.5 h / 0 - 20 °C / Inert atmosphere

3.2: 0.25 h / 20 °C / Inert atmosphere

4.1: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / 0.17 h / 0 - 20 °C / Inert atmosphere

5.1: dimethyl sulfoxide / 3 h / 60 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / toluene; dichloromethane / 0.25 h / -78 °C / Inert atmosphere

7.1: sodium tetrahydroborate / ethanol / 20 °C

8.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 20 °C

9.1: pyridinium p-toluenesulfonate / dichloromethane / 1 h / 0 °C / Inert atmosphere

9.2: 1 h / 0 - 20 °C / Inert atmosphere

10.1: diiodomethane; samarium / tetrahydrofuran / 4.5 h / 20 °C / Inert atmosphere; Darkness

11.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

12.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

12.2: Inert atmosphere

13.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 0.75 h / 0 - 20 °C / Inert atmosphere

14.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

15.1: toluene-4-sulfonic acid / methanol / 0.5 h / 0 - 20 °C / Inert atmosphere

16.1: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

17.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere

18.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

18.2: 0 °C / Inert atmosphere

18.3: 1.16 h / 0 - 20 °C / Inert atmosphere

19.1: N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

20.1: potassium hexamethylsilazane / toluene / 0.5 h / -78 °C / Inert atmosphere

21.1: diethyl ether; dibutyl ether / 0.25 h / 20 °C / Inert atmosphere

22.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 0 - 20 °C / Inert atmosphere

23.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere

23.2: 0.17 h / 90 °C / Inert atmosphere

With 1H-imidazole; samarium; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; diiodomethane; trifluorormethanesulfonic acid; iodine; diethylaluminium chloride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium chloride; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; dibutyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil; 2.1: |Diels-Alder Cycloaddition / 12.2: |Aldol Addition / 23.1: |Stille Carbonyl Synthesis;

DOI:10.1021/ja503899t

upstream raw materials:

C₁₀H₁₆O

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