4-Chlorobenzaldehyde → 2-Propenoic acid, 3-(4-chlorophenyl)-, ethyl ester

HRID 2174601Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:11]C([O-])=O>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:11][C:10]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 77264-Chlorobenzaldehyde

HCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 2014712-Propenoic acid, 3-(4-chlorophenyl)-, ethyl esterYield 89.9%

Procedure

4-Chlorobenzaldehyde (4.20 g, 30 mmol) and mono-ethyl malonate (4.60 ml, 39 mmol) were reacted as described under General Procedure A to furnish the title compound (5.68 g, 89%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.63 (d, J=16.0 Hz, 1H), 7.46-7.42 (m, 2H), 7.38-7.32 (m, 2H), 6.41 (d, J=16.0 Hz, 1H), 4.26 (q, J=7.2 Hz, 2H), 1.33 (t, J=7.2 Hz, 3H).

Sources & evidence

ORD record: ord-c38dad3870b448189295b85c0e8c79e2
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062013B2

Reaction notes

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