Dimethylformamide → 2-Chloro-4,6-dimethoxybenzaldehyde

HRID 1798050Notes

Reaction equation

HRID 1798050 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.CN([CH:15]=[O:16])C.O=P(Cl)(Cl)Cl>>[Cl:1][C:2]1[C:3]([CH:15]=[O:16])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 815021-Chloro-3,5-dimethoxybenzene

Product 1

HCID 38651392-Chloro-4,6-dimethoxybenzaldehydeYield 78.3%

Procedure

To a mixture of 5-chloro-1,3-dimethoxybenzene (25 g, 0.14 mol) in DMF (175 mL, 2.27 mol) at 0° C. was added POCl3 (42.5 mL, 0.46 mol) dropwise. The mixture was stirred at room temperature for 30 min and heated to reflux at 100° C. for an additional 2 h. The reaction mixture was poured onto ice and the yellow precipitate was collected by filtration, rinsed with cold water and dried under high vacuum to give a light yellow solid (22.7 g. Yield 78.3%). 1H NMR (400 MHz, CDCl3) δ0.43 (s, 1H), 6.59 (s, 1H), 6.42 (s, 1H), 3.92 (s, 3H), 3.89 (s, 3H); MS (ESI) m/z=201 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureto reflux at 100° C. for an additional 2 h
  3. additionThe reaction mixture was poured onto ice
  4. filtrationthe yellow precipitate was collected by filtration
  5. washrinsed with cold water
  6. customdried under high vacuum
  7. customto give a light yellow solid (22.7 g. Yield 78.3%)

Sources & evidence

ORD record
ord-15584918f35245019d9a0c506f7dcabd
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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