2,5-Diacetoxytoluene

Base Information

• Chemical Name: 2,5-Diacetoxytoluene
• CAS No.: 717-27-1
• Molecular Formula: C11H12O4
• Molecular Weight: 208.214
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID80400448
• Nikkaji Number: J993.892C
• Mol file: 717-27-1.mol

Synonyms:2,5-Diacetoxytoluene;717-27-1;Methylhydroquinone Diacetate;(4-acetyloxy-3-methylphenyl) acetate;2-methyl-1,4-phenylene diacetate;1,4-Diacetoxy-2-methylbenzene;Methylhydroquinone, diacetate;2-methylhydroquinone diacetate;2,5-Diacetoxytoluene, 97%;SCHEMBL2541390;KUZVIVNLNXNLAQ-UHFFFAOYSA-;DTXSID80400448;KUZVIVNLNXNLAQ-UHFFFAOYSA-N;MFCD00061098;(4-acetyloxy-2-methylphenyl) acetate;AKOS015889024;CS-0359302;D3318;FT-0628892;D90173;A837304;InChI=1/C11H12O4/c1-7-6-10(14-8(2)12)4-5-11(7)15-9(3)13/h4-6H,1-3H3

Chemical Property of 2,5-Diacetoxytoluene

Chemical Property:

• Vapor Pressure: 0.00217mmHg at 25°C
• Melting Point: 41-45 °C(lit.)
• Refractive Index: 1.505
• Boiling Point: 289.7 °C at 760 mmHg
• Flash Point: 140.2 °C
• PSA: 52.60000
• Density: 1.15 g/cm³
• LogP: 1.84560
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 208.07355886
• Heavy Atom Count: 15
• Complexity: 249

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,5-Diacetoxytoluene ^*data from reagent suppliers

Safty Information:

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)OC(=O)C)OC(=O)C
• Uses: 2,5-Diacetoxytoluene can be used to investigate the kinetics of co-?polyesters of hydroquinone diacetate and its methyl derivative. It is also a useful reagent to prepare regioselective O-?acylation of polyphenols.

Technology Process of 2,5-Diacetoxytoluene

There total 4 articles about 2,5-Diacetoxytoluene 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%

2-methylbenzene-1,4-diol (95-71-6,96937-50-7) + acetic anhydride (108-24-7) → 2,5-diacetoxytoluene (717-27-1)

Guidance literature:

With pyridine; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(03)00134-0

Reference yield: 99.0%

2-methylbenzene-1,4-diol (95-71-6,96937-50-7) + acetyl chloride (75-36-5) → 2,5-diacetoxytoluene (717-27-1)

Guidance literature:

With pyridine; In dichloromethane; at 25 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02228

Reference yield:

acetic anhydride (108-24-7) + 1-(1-trimethylsilyl-1,2-propadienyl)cyclopropanol → 2,5-diacetoxytoluene (717-27-1) + 2-methyl-3-trimethylsilyl-p-phenylene diacetate

Guidance literature:

With triethylamine; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, RT, 1 h, 2.) THF;

DOI:10.1246/cl.1995.115

upstream raw materials:

2-methylbenzene-1,4-diol

acetic anhydride

acetyl chloride

Downstream raw materials:

1-(2,5-dihydroxy-4-methylphenyl)ethanone

2,5-dihydroxybenzoic acid.

2-O-(α-methyl carboethoxy)-5-methoxy-4-methyl-acetophenone

4-hydroxy-3-methylphenyl acetate

Refernces

• 1、 Sarkar, Debayan,Ghosh, Manoj Kumar. "Stereoselective synthesis of Heliannuol G". supporting information. p. 4336 - 4339. Retrieved 2017/10/18.
• 2、 -. "Erratum: Biomimetic Total Synthesis of Paeoveitol (Org. Lett. (2016) 18: 18 (4578-4581) DOI: 10.1021/acs.orglett.6b02228)". supporting information. p. 6524 - 6524. Retrieved 2016/12/23.