Reaction #9403

Reaction equation

HCl

2,3,4-trimethoxybenzaldehyde

BCl3

sodium bicarbonate

→

purple solid

Yield 73.0%

2, 3-dihydroxy-4-methoxybenzaldehyde

Yield 73.0%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   OtherThe organic layer was separated
2. 2
   Extractionthe aq. layer was extracted with EtOAc (4×100 mL)
3. 3
   DryingThe organic layer was dried with MgSO4
4. 4
   Filtrationfiltered through celite
5. 5
   OtherAfter solvent evaporation
6. 6
   Otherthe crude mixture was recrystallized

Procedure

A dry CH2Cl2 (200 mL) solution of 2,3,4-trimethoxybenzaldehyde (19.6 g, 100 mmol), under nitrogen, was stirred for 10 min and BCl3 (1.0M solution in CH2Cl2, 200 mL) was added. The reaction was stirred for 24 hours and a 10% sodium bicarbonate solution (40 g/360 mL) was added. The resulting solution was acidified with concentrated HCl to PH 1. The organic layer was separated, and the aq. layer was extracted with EtOAc (4×100 mL). The organic layer was dried with MgSO4 and filtered through celite. After solvent evaporation, the crude mixture was recrystallized using (Hexanes/EtOAc:70/30) to afford 12.2 g (72.6 mmol, 73%) of a purple solid.

Source