α-Biotol

Base Information

• Chemical Name: α-Biotol
• CAS No.: 19902-26-2
• Molecular Formula: C15H24O
• Molecular Weight: 220.35
• Mol file: 19902-26-2.mol

Synonyms:α-Biotol;(1S)-2,3,4,5,6,7,8,8aβ-Octahydro-3β,8,8-trimethyl-6-methylene-1H-3aα,7α-methanoazulen-1β-ol

Chemical Property of α-Biotol

Chemical Property:

• Vapor Pressure: 6.92E-05mmHg at 25°C
• Boiling Point: 307°C at 760 mmHg
• Flash Point: 126.8°C
• Density: 1.02g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of α-Biotol

There total 27 articles about α-Biotol 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:

methyl exo-6-hydroxy-4,4,exo-8-trimethyl-3-(1-oxoethyl)-cis-bicyclo<3.3.0>octane-1-carboxylate (114626-88-9) → (+/-)-β-biotol (19902-26-2,114674-10-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / 2,6-Me₂C₅H₃N / CH₂Cl₂ / 0 °C

2: 96 percent / t-BuOK / 2-methyl-propan-2-ol / Heating

3: 1.) LiAlH₄; 2.) CrO₃; 3.) H₂ / 3.) Pd-C / 1.) Et₂O, heating; 2.) pyridine; 3.) EtOH

4: 95 percent / diethyl ether / Heating

5: 1.) SOCl₂, pyridine; 2.) 5 percent aq. HF / 1.) 0 deg C; 2.) MeCN, 0 deg C

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; lithium aluminium tetrahydride; thionyl chloride; hydrogen fluoride; potassium tert-butylate; hydrogen; palladium on activated charcoal; In diethyl ether; dichloromethane; tert-butyl alcohol;

DOI:10.1039/c39870001290

Reference yield:

methyl exo-6-acetoxy-4,4,exo-8-trimethyl-3-(1-oxoethyl)-cis-bicyclo<3.3.0>octane-1-carboxylate (118945-91-8) → (+/-)-β-biotol (19902-26-2,114674-10-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / K₂CO₃, MeOH

2: 98 percent / 2,6-Me₂C₅H₃N / CH₂Cl₂ / 0 °C

3: 96 percent / t-BuOK / 2-methyl-propan-2-ol / Heating

4: 1.) LiAlH₄; 2.) CrO₃; 3.) H₂ / 3.) Pd-C / 1.) Et₂O, heating; 2.) pyridine; 3.) EtOH

5: 95 percent / diethyl ether / Heating

6: 1.) SOCl₂, pyridine; 2.) 5 percent aq. HF / 1.) 0 deg C; 2.) MeCN, 0 deg C

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; methanol; lithium aluminium tetrahydride; thionyl chloride; hydrogen fluoride; potassium tert-butylate; hydrogen; potassium carbonate; palladium on activated charcoal; In diethyl ether; dichloromethane; tert-butyl alcohol;

DOI:10.1039/c39870001290

Reference yield:

dimethyl 3-acetoxy-exo-6-hydroxy-4,4,exo-8-trimethyl-cis-bicyclo<3.3.0>oct-2-ene-1,2-dicarboxylate (114626-84-5) → (+/-)-β-biotol (19902-26-2,114674-10-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 99 percent / K₂CO₃, MeOH

2: 62 percent / NaCl / H₂O; dimethylsulfoxide / Heating

3: 73 percent / CeCl₃ / tetrahydrofuran / -78 °C

4: 94 percent / HgO, 3 M H₂SO₄ / tetrahydrofuran

5: 65 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂

6: 91 percent / Bu₃SnH, AIBN / toluene / Heating

7: 100 percent / K₂CO₃, MeOH

8: 98 percent / 2,6-Me₂C₅H₃N / CH₂Cl₂ / 0 °C

9: 96 percent / t-BuOK / 2-methyl-propan-2-ol / Heating

10: 1.) LiAlH₄; 2.) CrO₃; 3.) H₂ / 3.) Pd-C / 1.) Et₂O, heating; 2.) pyridine; 3.) EtOH

11: 95 percent / diethyl ether / Heating

12: 1.) SOCl₂, pyridine; 2.) 5 percent aq. HF / 1.) 0 deg C; 2.) MeCN, 0 deg C

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; methanol; dmap; lithium aluminium tetrahydride; thionyl chloride; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); sulfuric acid; hydrogen fluoride; potassium tert-butylate; hydrogen; tri-n-butyl-tin hydride; potassium carbonate; sodium chloride; mercury(II) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol;

DOI:10.1039/c39870001290

upstream raw materials:

exo-4-(tert-butyldimethylsilyloxy)-exo-2,6,6,endo-8-tetramethyltricyclo<5.3.1.0^1.5>undecan-exo-8-ol

exo-4-(tert-butyldimethylsilyloxy)-exo-2,6,6-trimethyl-8-methylenetricyclo<5.3.1.0^1.5>undecane

methyl exo-6-hydroxy-4,4,exo-8-trimethyl-3-(1-oxoethyl)-cis-bicyclo<3.3.0>octane-1-carboxylate

exo-4-(tert-butyldimethylsilyloxy)-exo-2,6,6-trimethyltricyclo<5.3.1.0^1.5>undecan-8-one

Downstream raw materials:

(+/-)-α-biotol

Refernces

• 1、 Yates, Peter,Grewal, Rupinder S.,Hayes, Peter C.,Sawyer, Jeffery F.. "Synthesis of cedranoid sesquiterpenes. V. The biotols". . p. 2805 - 2815. Retrieved 2007/10/02.