Hydrochloric Acid → 2-Hydroxy-4,5-dimethoxybenzaldehyde

HRID 855907Notes

Reaction equation

HRID 855907 reaction equation
B(Cl)(Cl)Cl.C[O:6][C:7]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:8]=1[CH:9]=[O:10].C(=O)=O.CC(C)=O.Cl>C(Cl)Cl>[CH3:16][O:15][C:13]1[C:12]([O:17][CH3:18])=[CH:11][C:8]([CH:9]=[O:10])=[C:7]([OH:6])[CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 205252,4,5-TrimethoxybenzaldehydeHCID 25135Boron TrichlorideHCID 18522661Acetone cardice

Product 1

HCID 109869082-Hydroxy-4,5-dimethoxybenzaldehydeYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of boron trichloride (50 mL, 1.0 M solution in CH2Cl2) was slowly added to a solution of 2,4,5-trimethoxybenzaldehyde (3.92 g, 20 mmol) in CH2Cl2 (200 mL) at −78° C. (dry ice/acetone bath). The mixture was warmed to room temperature and stirred for three hours. 10 mL of HCl (37%) aqueous solution was poured into the resulting solution at 0° C. and extracted with CH2Cl2 (150 mL×3). The combined organic layer was washed with saturated aqueous NaCl (200 mL×2), water (100 mL×1), dried over MgSO4, and evaporated to afford 3.72 g of a light brown solid (3.72 g, 99%): 1H-NMR (400 MHz, CDCl3) δ3.88 (s, 3H), 3.94 (s, 3H), 6.47 (s, 1H), 6.91 (s, 1H), 9.70 (s, 1H).

Workup

  1. extractionextracted with CH2Cl2 (150 mL×3)
  2. washThe combined organic layer was washed with saturated aqueous NaCl (200 mL×2), water (100 mL×1)
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-ff47265027314f2c8b0a1e87b2ead4b4
Source dataset
uspto-grants-2007_08
Patent number
US07262301B1

Reaction notes

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