ChemicalBook CAS DataBase List 5-Ethynylisophthalic acid

5-Ethynylisophthalic acid synthesis

5synthesis methods

Product Name:5-Ethynylisophthalic acid
CAS Number:432025-97-3
Molecular formula:C10H6O4
Molecular Weight:190.15

313648-72-5 Synthesis

1,3-Benzenedicarboxylic acid, 5-[2-(triMethylsilyl)ethynyl]-, 1,3-diMethyl ester

313648-72-5
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432025-97-3
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Yield: 77%

Reaction Conditions:

Stage #1:dimethyl 5-(trimethylsilylethynyl)benzene-1,3-dicarboxylate with sodium hydroxide in tetrahydrofuran at 20; for 4 h;
Stage #2: with water;sodium hydroxide at 20; for 2 h;

Steps:

2
5-Ethynylisophthalic acid (4). 5-Ethynylisophthalic acid was prepared in one step by reacting dimethyl-5-(trimethylsilylethynyl)isophthaloate (3) (0.7 g, 3.2 mmol) with NaOH (1.412 g, 35.3 mmol) in THF (20 ml) at r. t. for 4 h. The precipitate formed was centrifuged down, dissolved in aq. NaOH (0.1 M, 50 ml) and stirred for 2 h at room temperature. The reaction mixture was cooled to 0° C. on an ice bath, acidified with 10% HCl to pH1-2. The precipitate formed was isolated by centrifugation, washed twice with water and dried, giving the target compound as a powder. Yield: 0.47 g, 77%.

References:

VINOGRADOV, Sergei A.;Esipova, Tatiana V. US2014/4048, 2014, A1 Location in patent:Paragraph 0089