4-ETHYNYL-BENZOIC ACID synthesis
- Product Name:4-ETHYNYL-BENZOIC ACID
- CAS Number:10602-00-3
- Molecular formula:C9H6O2
- Molecular Weight:146.14
75867-41-3
10602-00-3
Synthesis of 4-ethynylbenzoic acid: Methyl 4-[(trimethylsilyl)ethynyl]benzoate (714 mg, 3.07 mmol) was dissolved in a methanol solution of 4% KOH (w:v, 30 mL) and the reaction was carried out at reflux overnight. Upon completion of the reaction, the pH of the reaction solution was adjusted to 2-3 with 6N HCl (detected by pH paper), followed by extraction with ethyl acetate (EtOAc) twice. The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to afford 4-ethynylbenzoic acid (427 mg, 2.92 mmol, 95% yield) as a brown solid.1H-NMR (d6-acetone, 500 MHz) δ (ppm): 7.62 (d, J = 16.2 Hz, 2H); 8.03 (d, J = 16.3 Hz 2H).
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Yield:10602-00-3 77%
Reaction Conditions:
with lithium hydroxide in methanol;water for 2 h;
Steps:
21 Synthesis of Compound B 11
To a solution of 2 ( 0.5 g, 3.13 mmol) in MeOH (10 ml) was added LiOH (0.312 g. 12.52mmol) in water (10 ml). The mixture was stirred for 2 h then quenched by HCI solution (2N) extracted with EtOAc (30 ml x 3). The combined organic was dried over anhydrous Na2SO4 concentrated to give the desired intermediate 3 (0.35 g, 77%) as yellow solid.
References:
HANGZHOU ZYLOX PHARMA CO., LTD.;WANG, Bing;ZHAO, Jonathon Zhong WO2014/82286, 2014, A1 Location in patent:Paragraph 67
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