Reaction #595331

Reaction equation

4-hydroxybenzaldehyde

1-chloro-2-methyl-2-propanol

sodium carbonate

sodium bicarbonate

→

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

Solvents

DMF

ethyl acetate

Conditions

Workup

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

Procedure

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