4-Methylcatecholdimethylacetate

Base Information

• Chemical Name: 4-Methylcatecholdimethylacetate
• CAS No.: 52589-39-6
• Molecular Formula: C13H16O6
• Molecular Weight: 268.266
• Hs Code.: 2915900090
• DSSTox Substance ID: DTXSID001169811
• Nikkaji Number: J1.897.937C
• Mol file: 52589-39-6.mol

Synonyms:4-Methylcatecholdimethylacetate;methyl 2-[2-(2-methoxy-2-oxoethoxy)-4-methylphenoxy]acetate;(2-Methoxycarbonylmethoxy-5-methyl-phenoxy)-acetic acid methyl ester;2,2'-((4-methyl-1,2-phenylene)bis(oxy))bis-acetic acid dimethyl ester;DTXSID001169811;AKOS015889689;SB37513;FT-0640081;NS00007306;1,1'-Dimethyl 2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetate]

Chemical Property of 4-Methylcatecholdimethylacetate

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 39-41 °C
• Refractive Index: 1.499
• Boiling Point: 354.241 °C at 760 mmHg
• Flash Point: 154.606 °C
• PSA: 71.06000
• Density: 1.183 g/cm³
• LogP: 1.09860
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 268.09468823
• Heavy Atom Count: 19
• Complexity: 304

Purity/Quality:

99.9% ^*data from raw suppliers

(2-Methoxycarbonylmethoxy-5-methyl-phenoxy)-aceticacidmethylester 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)OCC(=O)OC)OCC(=O)OC
• Uses: Dimethyl 2,2''-((4-methyl-1,2-phenylene)bis(oxy))diacetate is used as a reactant in the preparation of Benzodioxepinones, useful as odorant agents for perfumes.

Technology Process of 4-Methylcatecholdimethylacetate

There total 2 articles about 4-Methylcatecholdimethylacetate 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: 90.0%

bromoacetic acid methyl ester (96-32-2) + 4-methyl-1,2-dihydroxybenzene (452-86-8) → 2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester (52589-39-6)

Guidance literature:

With potassium carbonate; In acetone; for 8h; Reflux;

DOI:10.1021/acs.inorgchem.8b03605

Reference yield: 83.0%

bromoacetic acid methyl ester (96-32-2) + 4-methyl-1,2-dihydroxybenzene (452-86-8) → 2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester (52589-39-6) + (2-hydroxy-4-methyl-phenoxy)-acetic acid methyl ester + (2-methoxycarbonylmethoxy-5-methyl-phenoxy)-acetic acid + (2-methoxycarbonylmethoxycarbonylmethoxy-4-methyl-phenoxy)-acetic acid methyl ester

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; microwave irradiation;

DOI:10.1016/j.tetlet.2004.11.045

Reference yield: 97.0%

2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester (52589-39-6) → 2-[2-(carboxymethyloxy)-4-methyl-phenoxy]acetic acid (5458-76-4)

Guidance literature:

With water; for 29h; Inert atmosphere; Reflux;

upstream raw materials:

bromoacetic acid methyl ester

4-methyl-1,2-dihydroxybenzene

Downstream raw materials:

4-methylcatechol

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1,2-bis(2-chloroethoxy)-4-methylbenzene

2-[2-(carboxymethyloxy)-4-methyl-phenoxy]acetic acid

Refernces

• 1、 -. "FORMATION AND USES OF EUROPIUM". Paragraph 0073. . Retrieved 2014/10/18.
• 2、 Drevermann, Britta,Lingham, Anthony R.,Huegel, Helmut M.,Marriott, Philip J.. "Synthesis of benzodioxepinone analogues via a novel synthetic route with qualitative olfactory evaluation". . p. 1006 - 1027. Retrieved 2008/02/04.