1-Methoxy-4-[(3-methylbut-3-en-1-yl)oxy]benzene

Base Information

• Chemical Name: 1-Methoxy-4-[(3-methylbut-3-en-1-yl)oxy]benzene
• CAS No.: 169310-73-0
• Molecular Formula: C12H16O2
• Molecular Weight: 192.258
• DSSTox Substance ID: DTXSID90451688
• Nikkaji Number: J3.541.757E
• Wikidata: Q82271834
• Mol file: 169310-73-0.mol

Synonyms:1-methoxy-4-[(3-methylbut-3-en-1-yl)oxy]benzene;169310-73-0;1-methoxy-4-(3-methylbut-3-enoxy)benzene;SCHEMBL18132995;DTXSID90451688;1-Methoxy-4-(3-methyl-3-butenyloxy)benzene;J3.541.757E

Chemical Property of 1-Methoxy-4-[(3-methylbut-3-en-1-yl)oxy]benzene

Chemical Property:

• Melting Point: 57-58 °C
• Boiling Point: 280.9±23.0 °C(Predicted)
• PSA: 18.46000
• Density: 0.969±0.06 g/cm3(Predicted)
• LogP: 3.04020
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 192.115029749
• Heavy Atom Count: 14
• Complexity: 169

Purity/Quality:

1-Methoxy-4-[(3-methyl-3-buten-1-yl)oxy]benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)CCOC1=CC=C(C=C1)OC
• Uses: 1-Methoxy-4-[(3-methyl-3-buten-1-yl)oxy]benzene is an intermediate in the synthesis of L-Isomer of Mevalonic acid (M339020), a precursor in the biosynthesis of cholesterol (C432501).

Technology Process of 1-Methoxy-4-[(3-methylbut-3-en-1-yl)oxy]benzene

There total 3 articles about 1-Methoxy-4-[(3-methylbut-3-en-1-yl)oxy]benzene 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: 100.0%

2-methyl-1-buten-4-ol (763-32-6) + 4-methoxy-phenol (150-76-5) → 1-methoxy-4-((3-methylbut-3-en-1-yl)oxy)benzene (169310-73-0)

Guidance literature:

With diethyl diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 20 ℃; for 1h; Heating / reflux;

Reference yield:

4-mesyloxy-2-methylbutene (80352-66-5) + 4-methoxy-phenol (150-76-5) → 1-methoxy-4-((3-methylbut-3-en-1-yl)oxy)benzene (169310-73-0)

Guidance literature:

4-mesyloxy-2-methylbutene; With potassium tert-butylate; In tetrahydrofuran; at 60 ℃; for 1h; Large scale;

4-methoxy-phenol; In tetrahydrofuran; at 60 ℃; for 16h; Large scale;

Reference yield:

2-methyl-1-buten-4-ol (763-32-6) → 1-methoxy-4-((3-methylbut-3-en-1-yl)oxy)benzene (169310-73-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 16 h / 10 - 25 °C / Large scale

2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 60 °C / Large scale

2.2: 16 h / 60 °C / Large scale

With potassium tert-butylate; triethylamine; In tetrahydrofuran; dichloromethane;

upstream raw materials:

2-methyl-1-buten-4-ol

4-methoxy-phenol

4-mesyloxy-2-methylbutene

Downstream raw materials:

(2S)-4-(4-methoxyphenoxy)-2-methylbutane-1,2-diol

(R)-2-(2-methyloxiran-2-yl)ethyl 4-methylbenzenesulfonate

C₁₇H₂₅BrO₅S

(R)-2-hydroxy-4-(4-methoxyphenoxy)-2-methylbutyl 4-methylbenzene-sulfonate

Refernces

• 1、 -. "Chiral heterocyclic tert-alcohol intermediate preparation method and application thereof". . . Retrieved 2018/11/04.
• 2、 Moodie, Lindon W. K.,Larsen, David S.. "A ring-closing enyne metathesis approach to functionalized semicyclic dienes: The total synthesis of (-)-tetrangomycin". . p. 1684 - 1694. Retrieved 2014/03/21.