ETHYL 1-HYDROXYCYCLOPENTANE-CARBOXYLATE Chemical Properties

Boiling point:

206℃

Density 

1.144

Flash point:

77℃

storage temp. 

2-8°C

pka

13.28±0.20(Predicted)

form 

liquid

color 

Yellow

InChI

InChI=1S/C8H14O3/c1-2-11-7(9)8(10)5-3-4-6-8/h10H,2-6H2,1H3

InChIKey

GINOXNRTFZITQJ-UHFFFAOYSA-N

SMILES

C1(O)(C(OCC)=O)CCCC1

Safety Information

HS Code 

2906190090

ETHYL 1-HYDROXYCYCLOPENTANE-CARBOXYLATE Usage And Synthesis

Uses

Ethyl 1-hydroxycyclopentanecarboxylate, is a building block used in synthesis of variious compounds such as spiromesifen (S683505), a useful insecticide and miticide in plant breeding. Also useful in cannabis testing kits as a component of pesticide mixes (P698240).

Synthesis

Concentrated sulfuric acid (catalytic amount) was added slowly to a solution of 1-hydroxycyclopentanecarboxylic acid (0.98 g, 7.5 mmol) in ethanol (3.8 mL). The reaction mixture was stirred at room temperature for 3 days. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure by rotary evaporator. The residue was dissolved in ethyl acetate (75 mL) and washed with saturated saline (25 mL). After separation of the organic layer, the aqueous layer was extracted once more with ethyl acetate (75 mL). All organic layers were combined and dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 1-ethoxycarbonyl-1-cyclopentanol (1.13 g, 95% yield) as a light brown oil. The mass spectrum (MS) showed m/z: 159 ([M + H]+).

References

[1] Patent: WO2015/124541, 2015, A1. Location in patent: Page/Page column 81
[2] Patent: CN106432163, 2017, A. Location in patent: Paragraph 0053-0055
[3] Journal of the Chemical Society, 1934, p. 946,954
[4] Collection of Czechoslovak Chemical Communications, 1963, vol. 28, p. 2520 - 2523
[5] Chimia, 2003, vol. 57, # 11, p. 697 - 701

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