Réaction #76348

Équation de réaction

Water

3-Hydroxybenzaldehyde

2-iodopropane

Potassium carbonate

→

3-isopropoxybenzaldehyde

Rendement 67.0%

Solvants

isopropanol

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was heated
2. 2
   Températureto reflux for 8 h, at which time TLC analysis
3. 3
   workup.DISSOLUTIONto dissolve all solids
4. 4
   Extractionthe mixture was extracted with ether (3×)
5. 5
   LavageThe combined ether layer was washed with water, 2 M NaOH, again with water until clear (4×)
6. 6
   SéchageThe solution was dried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Autreevaporated

Mode opératoire

Ex-645A) 3-Hydroxybenzaldehyde (5.60 g, 45.9 mmol) and 2-iodopropane (7.86 g, 46.2 mmol) were dissolved in 50 mL of isopropanol. Potassium carbonate (20 g, 145 mmol) was added, and the mixture was heated to reflux for 8 h, at which time TLC analysis indicated that the reaction had gone to completion. Water was added to dissolve all solids, and the mixture was extracted with ether (3×). The combined ether layer was washed with water, 2 M NaOH, again with water until clear (4×), and finally with brine. The solution was dried over MgSO4, filtered, and evaporated to give 5.03 g (67%) of the desired 3-isopropoxybenzaldehyde product as a pale oil. 1H NMR (C6D6) δ9.62 (s, 1H), 7.29 (s, 1H), 7.03 (m, 1H), 6.91 (t, 1H), 6.84 (m, 1H), 4.03 (septet, 1H), 0.96 (d, 6H).

Source