Cyclobutanecarboxylic acid, 3-methylene-, methyl ester (6CI,8CI,9CI) Chemical Properties

Boiling point:

56-59 °C(Press: 20 Torr)

Density 

1.01±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

liquid

color 

Clear, colourless

InChI

InChI=1S/C7H10O2/c1-5-3-6(4-5)7(8)9-2/h6H,1,3-4H2,2H3

InChIKey

OSWTXCSCDKIANQ-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2916200090

Cyclobutanecarboxylic acid, 3-methylene-, methyl ester (6CI,8CI,9CI) Usage And Synthesis

Synthesis

3-Methylenecyclobutanecarboxylic acid (11.0 g, 98.1 mmol) and potassium carbonate (27.1 g, 196 mmol) were dissolved in acetone (100 mL), and dimethyl sulfate (14.8 g, 117 mmol) was slowly added at 25 °C. The reaction mixture was heated to 70 °C and maintained for 12 hours. Upon completion of the reaction, water (20 mL) was added to quench the reaction, followed by extraction with dichloromethane (30 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to afford methyl 3-methylenecyclobutanecarboxylate (12.0 g, yellow oil) in 97% yield.

References

[1] Patent: CN105566324, 2016, A. Location in patent: Paragraph 0197; 0201; 0202; 0203
[2] Patent: WO2015/66413, 2015, A1. Location in patent: Page/Page column 131
[3] Patent: WO2012/154204, 2012, A1. Location in patent: Page/Page column 67; 68
[4] Patent: WO2015/180612, 2015, A1. Location in patent: Page/Page column 60
[5] Patent: WO2015/196071, A1. Location in patent: Paragraph 0174

Cyclobutanecarboxylic acid, 3-methylene-, methyl ester (6CI,8CI,9CI)(15963-40-3)Related Product Information

• Methyl 3-hydroxycyclobuta...
• METHYL 3-OXOCYCLOBUTANECARBOXYLATE
• BENZYL 3-OXOCYCLOBUTYLCARBAMATE
• T-butyl-3-oxocyclobutanecarboxylate
• 3-Hydroxy-cyclobutanecarboxylic acid ethyl ester
• 3-HYDROXYCYCLOBUTANECARBOXYLIC ACID
• tert-butyl 3-hydroxycyclobutanecarboxylate
• Carbamic acid, (3-oxocyclobutyl)-, 1,1-dimethylethyl ester (9CI)
• ETHYL 3-OXO CYCLOBUATNE CARBOXYLATE
• 3-Oxocyclobutanecarboxylic acid
• Cyclobutanecarboxylic acid