3-methoxycarbonylcyclopentane-1-carboxylic Acid

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3-methoxycarbonylcyclopentane-1-carboxylic Acid Basic information
Product Name:3-methoxycarbonylcyclopentane-1-carboxylic Acid
Synonyms:3-methoxycarbonylcyclopentane-1-carboxylic Acid;1,3-Cyclopentanedicarboxylicacid, 1-methyl ester;3-(Methoxycarbonyl)cyclopentanecarboxylic Acid
CAS:84545-00-6
MF:C8H12O4
MW:172.18
EINECS:
Product Categories:
Mol File:84545-00-6.mol
3-methoxycarbonylcyclopentane-1-carboxylic Acid Structure
3-methoxycarbonylcyclopentane-1-carboxylic Acid Chemical Properties
Boiling point 286.4±33.0 °C(Predicted)
density 1.242±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka4.51±0.40(Predicted)
AppearanceColorless to light yellow Liquid
Safety Information
MSDS Information
3-methoxycarbonylcyclopentane-1-carboxylic Acid Usage And Synthesis
Synthesis
NSC45401

6054-16-6

Sodium Methoxide

124-41-4

3-methoxycarbonylcyclopentane-1-carboxylic Acid

84545-00-6

To a methanolic (35 mL) suspension of 3-oxabicyclo[3.2.1]octane-2,4-dione (3.0 g, 21 mmol) was added sodium methanolate (1.2 g, 21 mmol) in batches at room temperature. After 1 h of reaction, the resulting clarified solution was evaporated, alkalized with 1 M NaOH solution and washed twice with ethyl acetate (EtOAc). Subsequently, the aqueous layer was acidified with 1N HCl to pH about 2 and extracted with dichloromethane (CH2Cl2, 3 x 25 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4) and evaporated to afford 3-(methoxycarbonyl)cyclopentane-1-carboxylic acid (2.7 g, 75%) as a clear oil. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.70 (s, 3H), 2.76-2.94 (m, 2H), 2.28 (dt, J = 13.3, 8.0 Hz, 1H), 2.15 (dt, J = 13.3, 9.1 Hz, 1H), 1.89-2.07 (m, 4H). The mass spectrum (APCI+) showed a m/z of 173.2 (C8H12O4, M+H)+.

References[1] Patent: WO2015/166373, 2015, A1. Location in patent: Page/Page column 147; 148
3-methoxycarbonylcyclopentane-1-carboxylic Acid Preparation Products And Raw materials
Raw materialsNSC45401-->Sodium Methoxide
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