3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)-

Base Information

• Chemical Name: 3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)-
• CAS No.: 95602-92-9
• Molecular Formula: C17H24O3
• Molecular Weight: 276.376
• DSSTox Substance ID: DTXSID20241897
• Mol file: 95602-92-9.mol

Synonyms:3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)-;3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-2-enoic acid;CBDivE_006353;DTXSID20241897;CTYWXRDQWMRIIM-UHFFFAOYSA-N;AM85670;NSC 226266;3,5-di-tert.-butyl-4-hydroxycinnamic acid;FT-0614735;FT-0614736;3,5-bis(1,1-dimethylethyl)-4-hydroxycinnamic acid;3-(3,5-di-t-butyl-4-hydroxyphenyl)prop-2-enoic acid

Chemical Property of 3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)-

Chemical Property:

• Melting Point: 213-214 °C(Solv: hexane (110-54-3); chloroform (67-66-3))
• Boiling Point: 375.4±37.0 °C(Predicted)
• PSA: 57.53000
• Density: 1.076±0.06 g/cm3(Predicted)
• LogP: 4.08500
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 276.17254462
• Heavy Atom Count: 20
• Complexity: 347

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C=CC(=O)O

Technology Process of 3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)-

There total 3 articles about 3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)- 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%

6,8-di-tert-butylspiro<4.5>-deca-1-oxa-5,8-diene-2,7-dione (82304-66-3) → 3,5-di-tert-butyl-4-hydroxycinnamic acid (95602-92-9)

Guidance literature:

With sulfuric acid; acetic acid; at 80 - 90 ℃; for 3h;

DOI:10.1007/BF00949806

Reference yield: 76.0%

malonic acid (141-82-2) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0) → 3,5-di-tert-butyl-4-hydroxycinnamic acid (95602-92-9)

Guidance literature:

With piperidine; pyridine; In benzene; at 80 ℃; for 6h;

DOI:10.1007/s10600-019-02772-x

Reference yield:

pyridine (110-86-1) + malonic acid (141-82-2) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0) → 3,5-di-tert-butyl-4-hydroxycinnamic acid (95602-92-9)

Guidance literature:

With piperidine;

DOI:10.1021/ja01575a051

upstream raw materials:

pyridine

malonic acid

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

6,8-di-tert-butylspiro<4.5>-deca-1-oxa-5,8-diene-2,7-dione

Downstream raw materials:

ethyl ester of trans-4-hydroxy-3,5-di-tert-butylcinnamic acid

2,6-di-tert-butyl-4-vinyl-phenol

(E)-3-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl>-2-propenoic acid hydrazide

(E)-2,6-bis(1,1-dimethylethyl)-4-{2-[5-(methylthio)-1,3,4-thiadiazol-2-yl]ethenyl}phenol

Refernces

• 1、 Dvornikova,Buravlev,Fedorova,Shevchenko,Chukicheva, I. Yu.,Kuchin. "Synthesis and Antioxidant Properties of Hydroxycinnamic Acid Derivatives Containing Isobornyl Substituents". . p. 658 - 664. Retrieved 2019.
• 2、 Robert,Robert-Piessard,Duflos,Le Baut,Khettab,Grimaud,Petit,Welin. "Non-acidic antiinfiammatory compounds II. Synthesis and activity of 6-amino-2,4-lutidine derivatives". . p. 841 - 854. Retrieved 2007/10/02.