(+/-)-4-epi-α-biotol

Base Information

• Chemical Name: (+/-)-4-epi-α-biotol
• CAS No.: 114674-11-2
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.355
• Mol file: 114674-11-2.mol

Synonyms:

Chemical Property of (+/-)-4-epi-α-biotol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-4-epi-α-biotol

There total 60 articles about (+/-)-4-epi-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: 93.0%

(+/-)-β-biotol (19902-26-2,114674-10-1) → (+/-)-α-biotol (19902-30-8,60371-70-2,114674-09-8,114674-11-2)

Guidance literature:

With hydrogen iodide; In water; benzene; at 30 ℃; for 24h;

DOI:10.1021/jo951955g

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) → (+/-)-α-biotol (19902-30-8,60371-70-2,114674-09-8,114674-11-2)

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-hydroxy-4,4,exo-8-trimethyl-3-(1-oxoethyl)-cis-bicyclo<3.3.0>octane-1-carboxylate (114626-88-9) → (+/-)-4-epi-α-biotol (19902-30-8,60371-70-2,114674-09-8,114674-11-2)

Guidance literature:

Multi-step reaction with 7 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

6: 100 percent / pyridinium chlorochromate / CH₂Cl₂

7: LiAlH₄ / diethyl ether / Heating

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

DOI:10.1039/c39870001290

upstream raw materials:

(+/-)-α-biotone

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

exo-4-(tert-butyldimethylsilyloxy)-exo-2,6,6,8-tetramethyltricyclo<5.3.1.0^1.5>undec-8-ene

Downstream raw materials:

(+/-)-4-epi-α-biotol

Refernces

• 1、 Chen, Yao-Jung,Chang, Wen-Hsin. "Stereocontrolled tandem radical cyclization: A new and facile route to syntheses of (±)-α-biotol and (±)-β-biotol". . p. 2536 - 2539. Retrieved 2007/10/03.
• 2、 Kuo,Yang,Chen,Lin. "The structure of 4 ketocedrol". . p. 686 - 687. Retrieved 2007/10/15.