ChemicalBook CAS DataBase List 3-Methoxybenzoylacetonitrile

3-Methoxybenzoylacetonitrile synthesis

11synthesis methods

Product Name:3-Methoxybenzoylacetonitrile
CAS Number:21667-60-7
Molecular formula:C10H9NO2
Molecular Weight:175.18

5368-81-0 Synthesis

5368-81-0
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75-05-8 Synthesis

75-05-8
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21667-60-7
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Yield: 83%

Reaction Conditions:

Stage #1:acetonitrile with lithium diisopropyl amide in tetrahydrofuran at -78; for 0.833333 h;
Stage #2:methyl 3-methoxybenzoate in tetrahydrofuran for 2.5 h;

Steps:

1a.1
LDA (44.2 ml. of a 2M solution in THF, 88.5 mmol) was added dropwise over 20 minutes to a cold (-78 ⁰C) solution of acetonitrile (2.8 ml_, 53.6 mmol) in THF (63 mL) under an atmosphere of nitrogen. The reaction mixture was stirred for 30 minutes and a solution of methyl 3-methoxybenzoate (7.00 g, 42.1 mmol) in THF (63 mL) was added dropwise over 30 minutes. The reaction mixture was stirred for 2 hours, quenched with a saturated aqueous solution of ammonium chloride (100 mL), allowed to warm to room temperature and diluted with Et₂O (300 mL). The aqueous layer was separated and extracted with Et₂O (100 mL). The combined organic layers were washed with 1 M HCI (200 mL), brine, dried (MgSO₄) and concentrated under reduced pressure. The residue was purified by column chromatography (25-30 % EtOAc in heptane) to afford the title compound as a pale orange solid (6.16 g, 83 % yield). ¹H NMR (300 MHz, CDCI₃) 7.50-7.42 (3H, m), 7.24-7.20 (1 H, m), 4.10 (2H, s), 3.89 (3H, s).

References:

Location in patent:Page/Page column 27