3-Hydroxy-cyclobutanecarboxylic acid ethyl ester Chemical Properties

Boiling point:

209℃

Density 

1.180

refractive index 

1.4504

Flash point:

83℃

storage temp. 

Inert atmosphere,Room Temperature

form 

liquid

color 

Clear Colourless

InChI

InChI=1S/C7H12O3/c1-2-10-7(9)5-3-6(8)4-5/h5-6,8H,2-4H2,1H3

InChIKey

KTVUZBJHOAPDGC-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2918300090

3-Hydroxy-cyclobutanecarboxylic acid ethyl ester Usage And Synthesis

Synthesis

General procedure for the synthesis of ethyl 3-hydroxycyclobutanecarboxylate from ethyl 3-oxocyclobutanecarboxylate: to a solution of ethyl 3-oxocyclobutanecarboxylate (0.18 g, 1.27 mmol) in methanol (10 mL) was slowly added sodium borohydride (0.048 g, 1.27 mmol) at 0 °C. The reaction mixture was stirred continuously at 0 °C for 30 min, followed by quenching the reaction with aqueous 1N hydrochloric acid. Volatile solvents were removed by distillation under reduced pressure and the residue was extracted by partitioning with ethyl acetate and 1N aqueous hydrochloric acid. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the target product ethyl 3-hydroxycyclobutanecarboxylate (0.17 g, 93% yield) as a mixture of cis and trans isomers. The product was characterized by 1H NMR (500 MHz, CDCl3), δ 4.17-4.24 (m, 1H), 4.15 (d, J=7.2 Hz, 2H), 2.54-2.66 (m, 3H), 2.11-2.22 (m, 2H), 1.27 (t, J=7.2 Hz, 3H).

References

[1] Patent: WO2016/40223, 2016, A1. Location in patent: Paragraph 00218
[2] Patent: WO2018/162607, 2018, A1. Location in patent: Paragraph 0769; 0770
[3] Patent: WO2016/24185, 2016, A1. Location in patent: Page/Page column 127
[4] Patent: US5681858, 1997, A
[5] Patent: WO2011/106273, 2011, A1. Location in patent: Page/Page column 72

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