(1E,3E)-1,3-Butadiene-1,4-dicarboxylic acid dimethyl ester synthesis

8synthesis methods

Product Name:(1E,3E)-1,3-Butadiene-1,4-dicarboxylic acid dimethyl ester
CAS Number:1119-43-3
Molecular formula:C8H10O4
Molecular Weight:170.16

(1E,3Z)-1,3-Butadiene-1,4-dicarboxylic acid dimethyl ester

692-92-2
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(1E,3E)-1,3-Butadiene-1,4-dicarboxylic acid dimethyl ester

1119-43-3
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Yield:1119-43-3 100%

Reaction Conditions:

iodine in acetonitrile; for 25 h;Product distribution / selectivity;Reflux;

Steps:

27

Example 27Synthesis of trans,trans Dimethyl Muconate from cis,trans Dimethyl Muconate A solution of cis,trans dimethyl muconate (0.60 g, 3.53 mmol) and a catalytic amount of iodine (43 mg, 4.8 mole percent) in acetonitrile (10 ml) is heated to reflux for 25 hours. The reaction is performed in the presence of ambient light in the laboratory. Removal of all solvent on a rotary evaporator is followed by applying a high vacuum, washing with 15 ml diethyl ether and hexane in a 3/2 volumetric ratio to remove all iodine, and drying under high vacuum yields an off-white crystalline solid (0.60 g, 3.53 mmol, 100 percent yield) which is identified as pure trans,trans dimethyl muconate.

References:

US2010/314243,2010,A1 Location in patent:Page/Page column 22