benzyl ether of (R)-(+)-(E)-6-isopropyl-3,9-dimethyl-5,8-decadien-1-ol

Base Information

• Chemical Name: benzyl ether of (R)-(+)-(E)-6-isopropyl-3,9-dimethyl-5,8-decadien-1-ol
• CAS No.: 82538-64-5
• Molecular Formula: C₂₂H₃₄O
• Molecular Weight: 314.511
• Mol file: 82538-64-5.mol

Synonyms:

Chemical Property of benzyl ether of (R)-(+)-(E)-6-isopropyl-3,9-dimethyl-5,8-decadien-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl ether of (R)-(+)-(E)-6-isopropyl-3,9-dimethyl-5,8-decadien-1-ol

There total 11 articles about benzyl ether of (R)-(+)-(E)-6-isopropyl-3,9-dimethyl-5,8-decadien-1-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:

methyl (R)-(+)-citronellate (20425-48-3) → benzyl ether of (R)-(+)-(E)-6-isopropyl-3,9-dimethyl-5,8-decadien-1-ol (82538-64-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) PhSeOH (generated in situ from PhSeSePh/H₂O₂), anh. MgSO₄, 2.) t-BuOOH / 1.) CH₂Cl₂, RT, 6 h, 2.) CH₂Cl₂, RT, 20 h

2: 1.) O₃, 2.) Me₂S / 1.) MeOH, -50 deg C, 2.) MeOH, -60 deg C to RT

3: TsOH / 1.5 h

4: 86.7 percent / LAH / diethyl ether / 1 h

5: 1.) NaH / 1.) DME, 65-70 deg C, 2 h, 2.) DME, reflux, 1 h, then RT

6: 35 percent HClO₄ / tetrahydrofuran / 0.5 h / Ambient temperature

7: tetrahydrofuran / 6 h / Ambient temperature

9: CrO_3.2C₅H₅N / CH₂Cl₂ / 0.67 h / Ambient temperature

10: tetrahydrofuran / -60 deg C to RT during 4.5 h

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; perchloric acid; dimethylsulfide; benzeneselenenic acid; dihydrogen peroxide; dipyridine chromium trioxide; sodium hydride; magnesium sulfate; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/0040-4020(82)80096-3

Reference yield:

methyl (3R)-3-methyl-5-oxopentanoate (79936-62-2) → benzyl ether of (R)-(+)-(E)-6-isopropyl-3,9-dimethyl-5,8-decadien-1-ol (82538-64-5)

Guidance literature:

Multi-step reaction with 8 steps

1: TsOH / 1.5 h

2: 86.7 percent / LAH / diethyl ether / 1 h

3: 1.) NaH / 1.) DME, 65-70 deg C, 2 h, 2.) DME, reflux, 1 h, then RT

4: 35 percent HClO₄ / tetrahydrofuran / 0.5 h / Ambient temperature

5: tetrahydrofuran / 6 h / Ambient temperature

7: CrO_3.2C₅H₅N / CH₂Cl₂ / 0.67 h / Ambient temperature

8: tetrahydrofuran / -60 deg C to RT during 4.5 h

With lithium aluminium tetrahydride; perchloric acid; dipyridine chromium trioxide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/0040-4020(82)80096-3

Reference yield:

(S)-(+)-5,5-dimethoxy-3-methyl-1-pentanol (82538-52-1) → benzyl ether of (R)-(+)-(E)-6-isopropyl-3,9-dimethyl-5,8-decadien-1-ol (82538-64-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DME, 65-70 deg C, 2 h, 2.) DME, reflux, 1 h, then RT

2: 35 percent HClO₄ / tetrahydrofuran / 0.5 h / Ambient temperature

3: tetrahydrofuran / 6 h / Ambient temperature

5: CrO_3.2C₅H₅N / CH₂Cl₂ / 0.67 h / Ambient temperature

6: tetrahydrofuran / -60 deg C to RT during 4.5 h

With perchloric acid; dipyridine chromium trioxide; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4020(82)80096-3

upstream raw materials:

triphenylphosphonio-1-methylethanide

(E)-8-benzyloxy-3-isopropyl-6-methyl-3-octenal

methyl (R)-(+)-citronellate

methyl (3R)-3-methyl-5-oxopentanoate

Refernces