5(4H)-Oxazolone, 4-((4-(acetyloxy)-3-methoxyphenyl)methylene)-2-methyl-

Base Information

• Chemical Name: 5(4H)-Oxazolone, 4-((4-(acetyloxy)-3-methoxyphenyl)methylene)-2-methyl-
• CAS No.: 39600-31-2
• Molecular Formula: C₁₄H₁₃NO₅
• Molecular Weight: 275.261
• Nikkaji Number: J422.403E
• Mol file: 39600-31-2.mol

Synonyms:4-((4-Acetoxy-3-methoxyphenyl)methylene)-2-methyl-2-oxazolin-5-one;39600-31-2;5(4H)-Oxazolone, 4-((4-(acetyloxy)-3-methoxyphenyl)methylene)-2-methyl-;5(4H)-Oxazolone, 4-[[4-(acetyloxy)-3-methoxyphenyl]methylene]-2-methyl-;SCHEMBL11716630;AHF102804;STK330574;AKOS003825970;2-methoxy-4-[(Z)-(2-methyl-5-oxo-1,3-oxazol-4(5H)-ylidene)methyl]phenyl acetate;2-Methoxy-4-[2-methyl-5-oxo-4,5-dihydro-1,3-oxazol-4-ylidene)methyl]phenyl acetate;2-methoxy-4-{[(4Z)-2-methyl-5-oxo-4,5-dihydro-1,3-oxazol-4-ylidene]methyl}phenyl acetate

Chemical Property of 5(4H)-Oxazolone, 4-((4-(acetyloxy)-3-methoxyphenyl)methylene)-2-methyl-

Chemical Property:

• Vapor Pressure: 5.12E-06mmHg at 25°C
• Boiling Point: 381.3°Cat760mmHg
• Flash Point: 166.7°C
• PSA: 74.19000
• Density: 1.26g/cm³
• LogP: 1.37220
• Solubility.: DCM
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 275.07937252
• Heavy Atom Count: 20
• Complexity: 468

Purity/Quality:

99% ^*data from raw suppliers

4-[[4-(Acetyloxy)-3-methoxyphenyl]methylene]-2-methyl-5(4H)-oxazolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC(=CC2=CC(=C(C=C2)OC(=O)C)OC)C(=O)O1
• Isomeric SMILES: CC1=N/C(=C\C2=CC(=C(C=C2)OC(=O)C)OC)/C(=O)O1
• Uses: 4-[[4-(Acetyloxy)-3-methoxyphenyl]methylene]-2-methyl-5(4H)-oxazolone is an intermediate towards the synthesis of Vanillactic Acid (V097200), an metabolite of dihydroxyphenylalanine (DOPA) (D533751, L-DOPA), which is an natural isomer of the immediate precursor of dopamine.

Technology Process of 5(4H)-Oxazolone, 4-((4-(acetyloxy)-3-methoxyphenyl)methylene)-2-methyl-

There total 3 articles about 5(4H)-Oxazolone, 4-((4-(acetyloxy)-3-methoxyphenyl)methylene)-2-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: 73.5%

→ 4-(4-acetoxy-3-methoxy-benzylidene)-2-methyl-4H-oxazol-5-one (60470-82-8,39600-31-2)

Guidance literature:

Reference yield: 50.0%

acetic anhydride (108-24-7) + vanillin (121-33-5,8014-42-4) + N-acetylglycine (543-24-8) → 4-(4-acetoxy-3-methoxy-benzylidene)-2-methyl-4H-oxazol-5-one (60470-82-8,39600-31-2)

Guidance literature:

With sodium acetate; at 95 - 135 ℃; for 9h;

DOI:10.1016/j.tet.2012.04.102

Reference yield:

vanillin acetate (881-68-5) + N-acetylglycine (543-24-8) → 4-(4-acetoxy-3-methoxy-benzylidene)-2-methyl-4H-oxazol-5-one (60470-82-8,39600-31-2)

Guidance literature:

With sodium acetate; acetic anhydride; at 120 ℃; for 8h; Inert atmosphere;

DOI:10.1002/ejoc.202101447

upstream raw materials:

acetic anhydride

vanillin

N-acetylglycine

vanillin acetate

Downstream raw materials:

Homovanillic acid

3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoic acid

3-methoxy-DL-tyrosine

(2RS,3RS)-2-acetylamino-2-chloro-3-hydroxy-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid