Hydrochloric Acid → 2,3-Dihydroxy-4-methoxybenzaldehyde

HRID 9307

Reaction equation

HRID 9307 reaction equation
C[O:2][C:3]1[C:10]([O:11]C)=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].B(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+].Cl>C(Cl)Cl>[OH:2][C:3]1[C:10]([OH:11])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25135Boron TrichlorideHCID 750062,3,4-TrimethoxybenzaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 115573522,3-Dihydroxy-4-methoxybenzaldehydeYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. customThe organic layer was separated
  2. extractionthe aq. layer was extracted with EtOAc (4×100 mL)
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered through celite
  5. customAfter solvent evaporation
  6. customthe crude mixture was recrystallized

Sources & evidence

ORD record
ord-9c5bd52821714c9bb9e8153a9d33262f
Source dataset
uspto-grants-2006_08
Patent number
US07091240B2

Linked notes

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