3-Methylbenzaldehyde → Ethyl 3-methylcinnamate

HRID 2174611Notes

Reaction equation

HRID 2174611 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:11]C([O-])=O>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH:11][C:10]([O:16][CH2:17][CH3:18])=[O:15]

Participants

3

Reactant 2

HCID 121053-MethylbenzaldehydeHCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 589327Ethyl 3-methylcinnamateYield 88%

Procedure

3-Methylbenzaldehyde (12.0 g, 100 mmol) and mono-ethyl malonate (15.5 ml, 130 mmol) were reacted as described under General Procedure A to furnish the title compound (16.7 g, 88%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.66 (d, J=16.0 Hz, 1H), 7.34-7.18 (m, 4H), 6.42 (d, J=16.0 Hz, 1H), 4.26 (q, J=7.2 Hz, 2H), 2.37 (s, 3H), 1.33 (t, J=7.2 Hz, 3H).

Sources & evidence

ORD record
ord-56299f5ecd4843b8b1513c91dce31529
Source dataset
uspto-grants-2015_06
Patent number
US09062013B2

Reaction notes

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