Benzene, 1-methoxy-4-[[[(3R)-3-methyl-4-pentynyl]oxy]methyl]-

Base Information

• Chemical Name: Benzene, 1-methoxy-4-[[[(3R)-3-methyl-4-pentynyl]oxy]methyl]-
• CAS No.: 158817-25-5
• Molecular Formula: C14H18O2
• Molecular Weight: 218.296
• DSSTox Substance ID: DTXSID80450483
• Nikkaji Number: J912.944H
• Wikidata: Q82270230
• Mol file: 158817-25-5.mol

Synonyms:158817-25-5;Benzene, 1-methoxy-4-[[[(3R)-3-methyl-4-pentynyl]oxy]methyl]-;DTXSID80450483;(3R)-3-Methyl-5-(4-methoxybenzyloxy)-1-pentyne

Chemical Property of Benzene, 1-methoxy-4-[[[(3R)-3-methyl-4-pentynyl]oxy]methyl]-

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 218.130679813
• Heavy Atom Count: 16
• Complexity: 220

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCOCC1=CC=C(C=C1)OC)C#C
• Isomeric SMILES: C[C@H](CCOCC1=CC=C(C=C1)OC)C#C

Technology Process of Benzene, 1-methoxy-4-[[[(3R)-3-methyl-4-pentynyl]oxy]methyl]-

There total 11 articles about Benzene, 1-methoxy-4-[[[(3R)-3-methyl-4-pentynyl]oxy]methyl]- 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: 87.0%

(3R)-1,1-dibromo-4-(4-methoxybenzyloxy)-3-methylpent-1-ene (158817-24-4) → (R)-1-methoxy-4-((3-methylpent-4-ynyloxy)methyl)benzene (158817-25-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 30h;

DOI:10.1246/cl.1994.1611

Reference yield:

(2R,3R)-5-p-methoxybenzyloxy-3-methylpentane-1,2-diol (158817-23-3) → (R)-1-methoxy-4-((3-methylpent-4-ynyloxy)methyl)benzene (158817-25-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NaIO₄ / tetrahydrofuran; H₂O / 0.17 h / Ambient temperature

2: 4.34 g / CBr₄, PPh₃ / CH₂Cl₂ / 0.33 h / 0 °C

3: 87 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

With sodium periodate; n-butyllithium; carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1016/S0040-4020(97)10253-8

Reference yield:

carbon tetrabromide (558-13-4) + (R)-4-(4-methoxybenzyloxy)-2-methylbutanal (320740-01-0) → (R)-1-methoxy-4-((3-methylpent-4-ynyloxy)methyl)benzene (158817-25-5)

Guidance literature:

carbon tetrabromide; (R)-4-(4-methoxybenzyloxy)-2-methylbutanal; With 2,6-dimethylpyridine; triphenylphosphine; In dichloromethane; at 0 ℃; for 1.5h; Inert atmosphere;

With n-butyllithium; In tetrahydrofuran; at -40 ℃; for 0.666667h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; Inert atmosphere;

DOI:10.1007/s11426-011-4454-0

upstream raw materials:

(3R)-1,1-dibromo-4-(4-methoxybenzyloxy)-3-methylpent-1-ene

3-(p-methoxybenzyloxy)propanal

p-methoxybenzyl chloride

3-(4-methoxybenzyl)oxypropan-1-ol

Downstream raw materials:

acetic acid 4-methoxy-2-[(R)-5-(4-methoxybenzyloxy)-3-methylpent-1-ynyl]phenyl ester

acetic acid 2-[(R)-5-hydroxy-3-methylpent-1-ynyl]-4-methoxyphenyl ester

2-[(R)-3-(5-Methoxy-benzofuran-2-yl)-butyl]-cyclohexane-1,3-dione

2-[(R)-3-(2,6-dimethoxycyclohexa-2,5-dienyl)-1-methylpropyl]-5-methoxybenzofuran