ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate Chemical Properties

Melting point:

33 °C

Boiling point:

183 °C(Press: 14 Torr)

Density 

1.167±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

10.69±0.20(Predicted)

Appearance

Colorless to light yellow Liquid

ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate Usage And Synthesis

Synthesis

GENERAL STEPS: Anhydrous THF (50 mL) solution of α-tetralone (6, 11.7 g, 80 mmol) was added slowly and dropwise under nitrogen protection to a stirred THF (150 mL) suspension of NaH (60%, 6.40 g, 160 mmol) and diethyl carbonate (150 mL). The reaction mixture was heated to reflux overnight and subsequently cooled in an ice bath and acidified with 1 M HCl (100 mL). The reaction solution was extracted with Et2O (3 × 200 mL), and the organic phases were combined, washed sequentially with NaHCO3 (200 mL) and brine (200 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give a light brown oily product (17.46 g, 99% yield), which could be used for the next reaction without further purification. The product was characterized by 1H NMR (400 MHz, CDCl3) and 13C NMR (100 MHz, CDCl3), and the data were consistent with those reported in the literature.

References

[1] European Journal of Organic Chemistry, 2016, vol. 2016, # 5, p. 918 - 920
[2] Tetrahedron Asymmetry, 2014, vol. 25, # 3, p. 238 - 244
[3] Journal of the American Chemical Society, 1986, vol. 108, p. 1617
[4] Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 1, p. 57 - 66
[5] Journal of Organic Chemistry, 2009, vol. 74, # 6, p. 2467 - 2475

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