Benzenebutanal, 3-methoxy-

Base Information

• Chemical Name: Benzenebutanal, 3-methoxy-
• CAS No.: 91152-86-2
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• DSSTox Substance ID: DTXSID00445316
• Nikkaji Number: J1.691.087B
• Wikidata: Q82263683
• Mol file: 91152-86-2.mol

Synonyms:4-(3-methoxyphenyl)butanal;Benzenebutanal, 3-methoxy-;91152-86-2;SCHEMBL8358192;4-(3-Methoxyphenyl)butyraldehyde;DTXSID00445316;QFHXCEIZIJQNBL-UHFFFAOYSA-N;1-(3-formylpropyl)-3-methoxybenzene;AKOS013845775;EN300-1847925

Chemical Property of Benzenebutanal, 3-methoxy-

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 145

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC(=C1)CCCC=O

Technology Process of Benzenebutanal, 3-methoxy-

There total 14 articles about Benzenebutanal, 3-methoxy- 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:

ethyl 4-(3'-methoxyphenyl)butyrate (57816-01-0) → 4-(3'-methoxyphenyl)butyraldehyde (91152-86-2)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃;

DOI:10.1021/ja045419u

Reference yield:

(3-methoxyphenyl)magnesium bromide (36282-40-3) → 4-(3'-methoxyphenyl)butyraldehyde (91152-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Li₂CuCl₄ / tetrahydrofuran

1.2: tetrahydrofuran / 0 - 20 °C

2.1: DIBAL-H / toluene; CH₂Cl₂ / -78 °C

With dilithium tetrachlorocuprate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja045419u

Reference yield:

formic acid (64-18-6) + 1-allyl-3-methoxybenzene (24743-14-4) → 2-(3-methoxyphenyl)butyraldehyde (1024039-14-2) + 3-methoxy-α-methyl-benzenepropanal (68383-30-2) + 4-(3'-methoxyphenyl)butyraldehyde (91152-86-2)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(1,5-cyclooctadiene)diiridium(I) dichloride; dicyclohexyl-carbodiimide; In acetonitrile; at 90 ℃; for 24h; Overall yield = 72 %; Overall yield = 64.3 mg; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.9b02047

upstream raw materials:

4-(3-methoxyphenyl)-1-butene oxide

4-(3-methoxyphenyl)butan-1-ol

ethyl 4-(3'-methoxyphenyl)butyrate

(3-methoxyphenyl)magnesium bromide

Downstream raw materials:

2-<8-(3-methoxyphenyl)-(E)-4-octenyl>-5-methylfuran

(E,Z)-1-methoxy-5-(3-methoxyphenyl)-1-pentene

1-[4'-(1,3-dioxolan-2''-yl)phenyl]-4-(3'''-methoxyphenyl)butan-1-ol

1-(4'-formylphenyl)-4-(3''-methoxyphenyl)butan-1-one