Water → 2-Hydroxy-4,5-dimethoxybenzaldehyde

HRID 1501523Notes

Reaction equation

HRID 1501523 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9](OC)[C:10]=1[O:11][CH3:12])[CH:6]=[O:7].B(Br)(Br)Br.[OH2:19]>C(Cl)Cl>[OH:19][C:8]1[CH:9]=[C:10]([O:11][CH3:12])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 68583,4,5-TrimethoxybenzaldehydeHCID 25134Boron tribromide

Product 1

HCID 109869082-Hydroxy-4,5-dimethoxybenzaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To solution of 3,4,5-trimethoxybenzaldehyde (5 g, 25.5 mmol) in CH2Cl2 (125 ml) at 0° C. was added BBr3 (6.39 g, 25.5 mmol). The resulting dark mixture was stirred at 0° C. for 10 hrs after completion of the reaction checked by TLC H2O (100 mL) was then added and the mixture was stirred for 10 min and the aqueous phase was extracted by CH2Cl2. The organic phase was dried over Na2SO4, and evaporated under reduced pressure. The resulting residue was purified by silica gel (CH2Cl2) afforded the 2-hydroxy 4,5dimethoxybenzaldehyde A1 (4.3 g) in 87% yield isolated yellow solid: 1H NMR (500 MHz, CDCl3) δ 11.33 (s, 1H), 9.63 (s, 1H), 6.83 (s, 1H), 6.40 (s, 1H), 3.87 (s, 3H), 3.81 (s, 3H) ppm. Mass: ESI [M+Na]+: 225.06; Elemental anal. calcd. for C9H10O4; C, 59.34; H, 5.53; O, 35.13. found C, 59.14; H, 5.13; O, 34.90.

Workup

  1. additionwas then added
  2. stirringthe mixture was stirred for 10 min
  3. extractionthe aqueous phase was extracted by CH2Cl2
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-3a4db0d4238942bebacc8b4c16cdbd0c
Source dataset
uspto-grants-2015_12
Patent number
US09206201B2

Reaction notes

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