ChemicalBook CAS DataBase List 2,6-DIMETHOXY-1,4-BENZOQUINONE

2,6-DIMETHOXY-1,4-BENZOQUINONE synthesis

15synthesis methods

Product Name:2,6-DIMETHOXY-1,4-BENZOQUINONE
CAS Number:530-55-2
Molecular formula:C8H8O4
Molecular Weight:168.15

134-96-3
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530-55-2
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$23.50/1g

Yield:530-55-2 73%

Reaction Conditions:

with [N,N'-bis(salicylidene)ethane-1,2-diaminato]cobalt(II);oxygen;triethylamine in methanol at 20; under 3102.97 Torr; for 24 h;

Steps:

Formation of 2-methoxybenzoquinone in the presence of a sterically hindered base.
General procedure: 5 mL of MeOH or CH₂Cl₂ were mixed in a Fisher-Potter bottle with 1 mmol of substrate, 0.1 mmol of catalyst and 1 mmol of hindered base. The vessel was pressurized to 60 psi with oxygen after flushing with the same gas, and the mixture was stirred for 24 hrs. The filtrate was evaporated under pressure and the residue was redisolved in a small amount of CH₂Cl₂ and passed through a silica column with 3:2 EtOAc:hexanes as the eluting solvent. 2-methoxy quinone elutes as a yellow fraction.

References:

Cedeno, Diana;Bozell, Joseph J. [Tetrahedron Letters,2012,vol. 53,# 19,p. 2380 - 2383] Location in patent:supporting information; experimental part

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