Réaction #595331

Équation de réaction

4-hydroxybenzaldehyde

1-chloro-2-methyl-2-propanol

sodium carbonate

sodium bicarbonate

→

4-(2-Hydroxy-2-methylpropoxy)benzaldehyde

Solvants

DMF

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Températureunder reflux for 24 h
2. 2
   AutreThe phases are separated
3. 3
   Séchagethe organic phase is dried over magnesium sulfate
4. 4
   AutreAfter removal of the solvent
5. 5
   Autrethe residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 5:1→1:1)
6. 6
   AutreThis gives a reddish solid which
7. 7
   Autreis used without further purification for the subsequent step

Mode opératoire

5.00 g (40.94 mmol) of 4-hydroxybenzaldehyde, 4.44 g (40.94 mmol) of 1-chloro-2-methyl-2-propanol and 6.08 g (57.32 mmol) of sodium carbonate are initially charged in 50 ml of dry DMF and stirred under reflux for 24 h. After cooling to RT, 20 ml of ethyl acetate and 20 ml of sat. aqueous sodium bicarbonate solution are added. The phases are separated, and the organic phase is dried over magnesium sulfate. After removal of the solvent, the residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 5:1→1:1). This gives a reddish solid which is used without further purification for the subsequent step.

Source