Ethanol → Ethyl (2-chlorobenzoyl)acetate

HRID 878487

Reaction equation

[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[O:20])[CH3:19].C(O)C>C1COCC1>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[O:20])[CH2:19][C:3]([O:7][CH2:8][CH3:9])=[O:10]

Participants

Conditions

Temperature: 40 °C

Procedure

Sodium hydride (1.45 g, 36 mmol) and diethyl carbonate (2.14 g, 18 mmol) were suspended in 10 ml of THF. 1-(2-Chlorophenyl)ethanone (1.4 g, 9 mmol) was gradually added into the reaction flask, maintaining the reaction mixture temperature at 40° C. for 2 h. Then 1 mL of ethanol was added thereto and heated under reflux conditions for 4 h. After cooling, 1 mL of ethanol was added and the mixture was poured onto ice water, and extracted with ether. Ether extracts are combined, washed with water, dried with anhydrous magnesium sulfate, and evaporated. The resulting oil is purified by flash column chromatography (PE/EA=50/1) to afford the title compound (680 mg, 34%) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.24 (3H, t, J=6.8 Hz), 4.03 (2H, s), 4.19 (2H, q, J=6.8 Hz), 7.31-7.36 (2H, m), 7.42-7.45 (2H, m). [M+H] Calc'd for C11H11ClO3, 227; Found, 227.

Workup

temperatureheated under reflux conditions for 4 h
temperatureAfter cooling
additionthe mixture was poured onto ice water
extractionextracted with ether
washwashed with water
dry with materialdried with anhydrous magnesium sulfate
customevaporated
customThe resulting oil is purified by flash column chromatography (PE/EA=50/1)

Sources & evidence

ORD record: ord-f0c6a6dd99594fe58aee20fba5547fd6
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987461B2

Linked notes

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