2-(2-CHLOROBENZYLOXY)BENZALDEHYDE synthesis
- Product Name:2-(2-CHLOROBENZYLOXY)BENZALDEHYDE
- CAS Number:53389-99-4
- Molecular formula:C14H11ClO2
- Molecular Weight:246.69
90-02-8
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53389-99-4
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Yield: 84%
Reaction Conditions:
with potassium carbonate;potassium iodide in ethanol at 85;
Steps:
Synthesisof intermediate 3-8, 30, 32, 34 and 38:
General procedure: To a solution of the different substituted hydroxybenzaldehyde (2a-2e) (4 mmol) in ethanol (30 ml), K2CO3(1 eq), KI (1 eq) and substituted benzyl chloride (1a-1e) (4 mmol) were added at room temperature. The reactionmixture was refluxed at 85°C for 4-8 hours. After completion, the solvent wasremoved in vacuo. Water (100 ml) was added and the mixture was extracted withethyl acetate, and evaporated. The crude oil was puried by columnchromatography over silica gel (petroleum ether : ethyl acetate = 20:1), as awhite solid, yield 63%-87%. 2-((2-Chlorobenzyl)oxy)benzaldehyde(intermediate 3) white solid, yield84%, 1H NMR (400 MHz, DMSO-d6), δ (ppm):10.40 (d, J = 0.6 Hz, 1H), 7.74 - 7.71 (m, 1H), 7.67 (ddd, J =8.4, 5.9, 3.9 Hz, 2H), 7.53 - 7.50 (m, 1H), 7.39 (dd, J = 5.8, 3.5 Hz,2H), 7.34 (d, J = 8.3 Hz, 1H), 7.11 (t, J = 7.5 Hz, 1H), 5.32 (s,2H). 13C NMR (100 MHz, DMSO-d6), δ (ppm):189.1, 160.4, 136.4, 133.7, 132.6, 130.2, 130.1, 129.5, 128.0, 127.5, 124.7,121.3, 114.1, 67.7.
References:
Zhao, Shuangmei;Zhen, Yongqi;Fu, Leilei;Gao, Feng;Zhou, Xianli;Huang, Shuai;Zhang, Lan [Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,# 19,art. no. 126623] Location in patent:supporting information
89-95-2
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611-19-8
432 suppliers
$7.00/25g
53389-99-4
36 suppliers
$20.00/500mg