ChemicalBook CAS DataBase List 2-HYDROXY-4-IODO-BENZALDEHYDE

2-HYDROXY-4-IODO-BENZALDEHYDE synthesis

10synthesis methods

Product Name:2-HYDROXY-4-IODO-BENZALDEHYDE
CAS Number:38170-02-4
Molecular formula:C7H5IO2
Molecular Weight:248.02

50-00-0 Synthesis

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533-58-4 Synthesis

533-58-4
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38170-02-4
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Yield: 79%

Reaction Conditions:

with triethylamine;magnesium chloride in acetonitrile at 10 - 72; for 2 h;

Steps:

3.1
4-(nitrooxy)butyl (2R)-7-benzyl-6-chloro-2-(trifluoromethyl)-2H-chromene-3- carboxylate; Step 1; Preparation of 2-hydroxy-4-iodobenzaldehyde; [0168] To a chilled solution of commercially available 2-iodophenol (30 g, 136 mmole) in ACN was added MgCl₂ (19.5 g, 204 mmole) portion-wise while maintaining the temperature below 10 ⁰C, followed by paraformaldehyde (28.6 g, 954 mmole) and TEA (76 mL, 545 mmole) producing a 15 °C exotherm. The solution was heated to 72 ⁰C for 2 h. The reaction was cooled to room temperature and poured into Saturated aqueous Ammonium Chloride (500 mL), extracted with ethyl acetate (2 X 150 mL). The combined organic phases were washed with aqueous NaHCO₃ solution (2 X 150 mL), aqueous IN HCl solution (2 X 150 mL), and brine (2 X 150 mL), dried over Na₂SO₄, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 5% Ethyl acetate/ Hexane). Desired fractions were collected and combined, removed solvent in vacuo producing the ethyl ester (27 g, 79%) as a yellow solid. This salicylaldehyde was of suitable purity to use without further purification.

References:

PHARMACIA & UPJOHN COMPANY LLC WO2006/40676, 2006, A1 Location in patent:Page/Page column 51

50-00-0 Synthesis

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