3-HYDROXYCYCLOBUTANECARBOXYLIC ACID Chemical Properties

Boiling point:

290.1±33.0 °C(Predicted)

Density 

1.45g/ml

storage temp. 

2-8°C

pka

4.54±0.40(Predicted)

form 

solid

color 

White

InChI

InChI=1S/C5H8O3/c6-4-1-3(2-4)5(7)8/h3-4,6H,1-2H2,(H,7,8)

InChIKey

ZSHGVMYLGGANKU-UHFFFAOYSA-N

SMILES

C1(C(O)=O)CC(O)C1

Safety Information

RIDADR 

UN2811

HS Code 

2918199890

3-HYDROXYCYCLOBUTANECARBOXYLIC ACID Usage And Synthesis

Uses

3-Hydroxycyclobutylcarboxylic acid and its derivatives are important pharmaceutical intermediates widely used in drug synthesis. For example, they are used to synthesize the clinically widely used anti-inflammatory and analgesic loxoprofen sodium, the bactericide tebuconazole, and the side chain of the broad-spectrum antibacterial drug cefpirome. 3-Hydroxycyclobutylcarboxylic acid is mainly used in the preparation of antiviral and antitumor drugs, and also has wide applications in the design and development of novel functional polymers, specialty surfactants, and high-performance lubricants.

Synthesis

General procedure for the synthesis of 3-hydroxycyclobutanecarboxylic acid from methyl 3-hydroxycyclobutanecarboxylate: cis-3-hydroxycyclobutanecarboxylic acid methyl ester (273.3 g, 2.1 mol, 1 eq.) was dissolved in a mixed solvent of H2O/THF (1 L/1.5 L), followed by addition of lithium hydroxide monohydrate (218.2 g, 5.2 mol, 2.5 eq.). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, THF was removed by distillation under reduced pressure. the pH of the reaction solution was adjusted to 4~5 with dilute hydrochloric acid, and then extracted with a chloroform/isopropanol solvent mixture in the ratio of 4:1 by volume. The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by ethyl acetate/n-heptane mixed solvent pulping to afford 3-hydroxycyclobutanecarboxylic acid (197.4 g, 1.7 mol) in off-white solid form with 81% yield and 97% purity.

References

[1] Patent: CN107903161, 2018, A. Location in patent: Paragraph 0033; 0034

3-HYDROXYCYCLOBUTANECARBOXYLIC ACID(194788-10-8)Related Product Information

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• 3,3-Dimethoxycyclobutane-1-carboxylate methyl ester
• 1-AMINO-3-BENZYLOXYCYCLOBUTANE-1-CARBOXYLIC ACID
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• AURORA KA-784