Phosphorus oxychloride → 2,3,4,5-Tetramethoxybenzaldehyde

HRID 1527671Notes

Reaction equation

HRID 1527671 reaction equation
CN([CH:9]=[O:10])C1C=CC=CC=1.O=P(Cl)(Cl)Cl.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[C:19]=1[O:28][CH3:29]>C(Cl)Cl.CCOC(C)=O>[CH3:16][O:17][C:18]1[C:19]([O:28][CH3:29])=[C:20]([O:26][CH3:27])[C:21]([O:24][CH3:25])=[CH:22][C:23]=1[CH:9]=[O:10]

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 6077731,2,3,4-Tetramethoxybenzene

Product 1

HCID 6394122,3,4,5-TetramethoxybenzaldehydeYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure by Syper et al.,19 N-methylformanilide (1.0 mL, 8.1 mmol) was added to a flame dried 10 mL round bottom flask under argon and a drying tube. POCl3 (1.0 mL, 11 mmol) was added at room temperature and the Argon line was removed. After 5 minutes 18 (1.067 g, 5.38 mmol) was dissolved in CH2Cl2 (2.0 mL) and added at room temperature. The reaction was stirred at room temperature under a drying tube for 48 hrs and monitored by 1H NMR. When complete the reaction was diluted with EtOAc, washed with saturated brine, dried over MgSO4, filtered, and condensed. The resulting product was separated from remaining N-methylformanilide using flash chromatography (1:4 Et2O:hexanes) to provide 19 (1.141 g, 5.04 mmol, 94%) as a colorless oil.

Workup

  1. additionwas added to a flame
  2. customdried 10 mL round bottom flask under argon
  3. customthe Argon line was removed
  4. additionadded at room temperature
  5. washwashed with saturated brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customcondensed
  9. customThe resulting product was separated

Sources & evidence

ORD record
ord-c2c45e8f3a8348619eda0bf1daeb2587
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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