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

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ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate Basic information
Product Name:ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
Synonyms:ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate;2-Naphthalenecarboxylic acid, 1,2,3,4-tetrahydro-1-oxo-, ethyl ester;ethyl 1-oxo-3,4-dihydro-2H-naphthalene-2-carboxylate
CAS:6742-26-3
MF:C13H14O3
MW:218.25
EINECS:
Product Categories:
Mol File:6742-26-3.mol
ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate Structure
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
pka10.69±0.20(Predicted)
AppearanceColorless to light yellow Liquid
Safety Information
MSDS Information
ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate Usage And Synthesis
Synthesis
1-Tetralone

529-34-0

Diethyl carbonate

105-58-8

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

6742-26-3

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
ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate Preparation Products And Raw materials
Raw materialsETHYL 2-IODOBENZOATE-->Diethyl carbonate-->1-Tetralone-->Tetrahydrofuran-->Sodium hydride
Preparation ProductsMethyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate
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