Cyclobutanecarboxylic acid, 3-hydroxy-, methyl ester Chemical Properties

Boiling point:

190℃

Density 

1.232

Flash point:

76℃

storage temp. 

2-8°C

pka

14.73±0.40(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C6H10O3/c1-9-6(8)4-2-5(7)3-4/h4-5,7H,2-3H2,1H3

InChIKey

BYKHAEUVLSBWSU-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2918999090

Cyclobutanecarboxylic acid, 3-hydroxy-, methyl ester Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 3-hydroxycyclobutanecarboxylate from methyl 3-carbonyl-cyclobutanecarboxylate: Methyl 3-carbonyl-cyclobutanecarboxylate (307.5 g, 2.4 mol, 1.0 eq.) was dissolved in 3 L of tetrahydrofuran and the solution was cooled down to -78 to -60 °C. Subsequently, 3.5 L of tetrahydrofuran solution of lithium hydrogenated tri-tert-butoxyaluminum (915.4 g, 3.6 mol, 1.5 eq.) was added slowly and dropwise. After 3 hours of reaction, the completion of the reaction was confirmed by TLC. Then, 1 L of 2.5 mol/L hydrochloric acid was added dropwise to terminate the reaction and the pH of the reaction solution was adjusted to about 6 while the temperature was controlled at about 0 °C. The reaction mixture was diluted by adding 3 L of ethyl acetate and stirred for 30 minutes. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed three times with ethyl acetate. The filtrate was separated and the aqueous phase was extracted with ethyl acetate. All organic phases were combined and concentrated by drying to give a yellow liquid methyl cis-3-hydroxycyclobutanecarboxylate (273.3 g, 2.1 mol) in 88% yield and 95% purity.

References

[1] Patent: CN107903161, 2018, A. Location in patent: Paragraph 0025; 0026; 0027; 0028; 0029; 0030; 0031; 0032
[2] Patent: WO2017/48675, 2017, A1. Location in patent: Paragraph 0480
[3] Patent: CN106478651, 2017, A. Location in patent: Paragraph 1112; 1113; 1114
[4] Patent: CN104447583, 2016, B. Location in patent: Paragraph 0160; 0161; 0162
[5] Patent: CN104447747, 2016, B. Location in patent: Paragraph 0176-0177

Cyclobutanecarboxylic acid, 3-hydroxy-, methyl ester(4934-99-0)Related Product Information

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