Acetic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-4,5-dihydro-isoxazol-5-yl ester

Base Information

• Chemical Name: Acetic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-4,5-dihydro-isoxazol-5-yl ester
• CAS No.: 179461-35-9
• Molecular Formula: C₁₉H₂₇NO₄
• Molecular Weight: 333.428
• DSSTox Substance ID: DTXSID101320830
• ChEMBL ID: CHEMBL1905731
• Mol file: 179461-35-9.mol

Synonyms:MLS000777080;CHEMBL1905731;DTXSID101320830;HMS2751E23;STL569941;AKOS030508696;179461-35-9;SMR000413378;[3-(3,5-ditert-butyl-4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl] acetate;3-(3,5-DI-TERT-BUTYL-4-HYDROXYPHENYL)-4,5-DIHYDRO-1,2-OXAZOL-5-YL ACETATE;Acetic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-4,5-dihydro-isoxazol-5-yl ester

Chemical Property of Acetic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-4,5-dihydro-isoxazol-5-yl ester

Chemical Property:

• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 333.19400834
• Heavy Atom Count: 24
• Complexity: 477

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1CC(=NO1)C2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C

Technology Process of Acetic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-4,5-dihydro-isoxazol-5-yl ester

There total 2 articles about Acetic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-4,5-dihydro-isoxazol-5-yl ester 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:

3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0) → Acetic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-4,5-dihydro-isoxazol-5-yl ester (179461-35-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85.6 percent / NH₂OH*HCl

2: 1.) N-chlorosuccinimide, 2.) Et₃N / 1.) DMF, 40 deg C, 1 h, 2.) 20 deg C, 1 h

With N-chloro-succinimide; hydroxylamine hydrochloride; triethylamine;

DOI:10.1007/BF01433983

Reference yield:

vinyl acetate (108-05-4,9003-20-7) + 3,5-di-tert-butyl-4-hydroxybenzaldehyde oxime (787-13-3) → Acetic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-4,5-dihydro-isoxazol-5-yl ester (179461-35-9) + 2,5-di-(4'-hydroxy-3',5'-di-tert-butylphenyl)-1,4-dioxa-3,6-diazine

Guidance literature:

With N-chloro-succinimide; triethylamine; Yield given. Multistep reaction. Yields of byproduct given; 1.) DMF, 40 deg C, 1 h, 2.) 20 deg C, 1 h;

DOI:10.1007/BF01433983

Reference yield: 93.0%

Acetic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-4,5-dihydro-isoxazol-5-yl ester (179461-35-9) → 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)-5-hydroxyisoxazoline-2 (179461-40-6)

Guidance literature:

With potassium hydroxide; In methanol; for 1h; Heating;

DOI:10.1007/BF01433983

upstream raw materials:

vinyl acetate

3,5-di-tert-butyl-4-hydroxybenzaldehyde oxime

3,5-di-t-butyl-4-hydroxybenzaldehyde

Downstream raw materials:

3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)-5-hydroxyisoxazoline-2