ChemicalBook CAS DataBase List 3-HYDROXY-4-IODOBENZALDEHYDE

3-HYDROXY-4-IODOBENZALDEHYDE synthesis

4synthesis methods

Product Name:3-HYDROXY-4-IODOBENZALDEHYDE
CAS Number:135242-71-6
Molecular formula:C7H5IO2
Molecular Weight:248.02

100-83-4
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$5.00/10g

135242-71-6
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$34.00/250mg

Yield:135242-71-6 28%

Reaction Conditions:

with ammonium hydroxide;iodine;potassium iodide in water at 20; for 2 h;

Steps:

3-Hydroxy-4-iodobenzaldehyde (5)
3-Hydroxybenzaldehyde (1.60 g, 13.18 mmol) was dissolved in 15 mL of 33% aqueousNH4OH in a 100 mL round-bottomed flask. Separately, iodine (3.72 g,14.65 mmol) was added to 25 mL of 30% (w/v) solution of KI in water. The lattersolution was added dropwise to the 3-hydroxybenzaldehyde solution, after which thereaction was stirred at rt for 2h. The reaction mixture was cooled then with an icebath and made acid with conc. HCl, which caused the appearance of a yellow gum.The gum was taken up in Et2O, and the remaining aqueous solution was extractedwith more Et2O (3 £ 10 mL). The organic layers were pooled together, washed with10 mL of an aqueous saturated solution of Na2S2O3, and dried over anh. Na2SO4.After filtration and solvent removal under reduced pressure, an orange-colored solidis obtained, which was crystallized from Et2O to afford 927 mg of 3-hydroxy-4-iodobenzaldehyde5 as a yellowish solid. Yield: 28%. M.p.: 128-130C, lit. mp. 128-129 C.25 1H RMN (300 MHz, CD3COCD3): d 9.94 (s, 1H), 9.67 (s, 1H), 8.00 (d, JD 8.0 Hz, 1H), 7.41 (d, J D 1.8 Hz, 1H), 7.20 (dd, J1 D 8.0 Hz, J2 D 1.8 Hz, 1H);1H RMN (300 MHz, CDCl3) d ppm: 9.92 (s, 1H), 7.88 (d, J D 8.1 Hz, 1H), 7.44 (d,J D 1.8 Hz, 1H), 7.18 (dd, J1 D 8.1 Hz, J2 D 1.8 Hz, 1H), 5.93 (br s, 1H); 13CRMN (75 MHz, CD3COCD3): d 193.2 (CHO), 159.2 (C-3), 142.1 (C-5), 140.2 (C-1),124.5 (C-6), 115.3 (C-2), 94.0 (C-4); 13C RMN (75 MHz, CDCl3): d 191.3 (CHO),155.8 (C-3), 139.3 (C-5), 138.3 (C-1), 123.0 (C-6), 114.8 (C-2), 93.9 (C-4); HRMS(EI) m/z: Calcd for C7H5IO2: 247.9334. Found: 247.9358.

References:

Blasco, Raül;de Arellano, Carmen Ramírez;Sanz-Cervera, Juan F. [Organic Preparations and Procedures International,2017,vol. 49,# 3,p. 265 - 272]

FullText

773869-57-1 Synthesis