(E)-4-(2-Hydroxy-3-methoxyphenyl)but-3-en-2-one

Base Information

• Chemical Name: (E)-4-(2-Hydroxy-3-methoxyphenyl)but-3-en-2-one
• CAS No.: 22214-32-0
• Molecular Formula: C11H12O3
• Molecular Weight: 192.214
• ChEMBL ID: CHEMBL72918
• DSSTox Substance ID: DTXSID801240308
• Nikkaji Number: J1.796.261B,J2.202.021H
• Mol file: 22214-32-0.mol

Synonyms:22214-32-0;(E)-4-(2-Hydroxy-3-methoxyphenyl)but-3-en-2-one;ortho-Dehydrozingerone;4-(2-Hydroxy-3-methoxyphenyl)but-3-en-2-one;CHEMBL72918;SCHEMBL11260283;DTXSID801240308;EN300-1835570;(3E)-4-(2-Hydroxy-3-methoxyphenyl)-3-buten-2-one;4-(2'-hydroxy-3'-methoxyphenyl)-(e)-3-buten-2-one

Chemical Property of (E)-4-(2-Hydroxy-3-methoxyphenyl)but-3-en-2-one

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 192.078644241
• Heavy Atom Count: 14
• Complexity: 223

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C=CC1=C(C(=CC=C1)OC)O
• Isomeric SMILES: CC(=O)/C=C/C1=C(C(=CC=C1)OC)O

Technology Process of (E)-4-(2-Hydroxy-3-methoxyphenyl)but-3-en-2-one

There total 4 articles about (E)-4-(2-Hydroxy-3-methoxyphenyl)but-3-en-2-one 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: 81.0%

3-methoxy-2-hydroxybenzaldehyde (148-53-8) + acetone (67-64-1) → (E)-1-(2'-hydroxy-3'-methoxyphenyl)but-1-en-3-one (22214-32-0)

Guidance literature:

With 1-n-butyl-3-methylimidazolim bromide; at 60 ℃; for 6h; Enzymatic reaction;

DOI:10.1002/adsc.201000870

Reference yield:

C11H14O4 (1162641-94-2) → (E)-1-(2'-hydroxy-3'-methoxyphenyl)but-1-en-3-one (22214-32-0)

Guidance literature:

With hydrogenchloride; In water; at 60 ℃; for 1h;

DOI:10.1021/acs.joc.6b01899

Reference yield:

C6H5COC3H6OCH3O (113842-30-1) → (E)-1-(2'-hydroxy-3'-methoxyphenyl)but-1-en-3-one (22214-32-0)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium dichloride; chromium(VI) oxide / acetonitrile; water / 60 °C

2: hydrogenchloride / water / 1 h / 60 °C

With chromium(VI) oxide; hydrogenchloride; palladium dichloride; In water; acetonitrile; 1: |Wacker Oxidation;

DOI:10.1021/acs.joc.6b01899

upstream raw materials:

3-methoxy-2-hydroxybenzaldehyde

acetone

C₆H₅COC₃H₆OCH₃O

C₁₁H₁₄O₄

Downstream raw materials:

1-acetyl-2-(2'-hydroxy-3'-methoxyphenyl)cyclopropane

3-<4'-hydroxy-3'-methyl'-2'(E)-butenyl>-7-methoxy-2,3-dihydrobenzofuran

2-(2'-hydroxy-3'-methoxyphenyl)-5-methyl-3,6-dihydro-6H-pyran

7-methoxy-3-<2'-methyl-2',3'-methylene-3'-(methylsulphinyl)propyl>-2,3-dihydrobenzofuran