Dimethylformamide → 3-Isopropyl-4-methoxybenzaldehyde

HRID 1392550Notes

Reaction equation

HRID 1392550 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11])([CH3:3])[CH3:2].O=P(Cl)(Cl)Cl.CN([CH:20]=[O:21])C>>[CH:20]([C:8]1[CH:7]=[CH:6][C:5]([O:10][CH3:11])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:9]=1)=[O:21]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 2706232-Isopropylanisole

Product 1

HCID 98989903-Isopropyl-4-methoxybenzaldehydeYield 84.5%

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 2-isopropylanisole (859 g, 5.85 mol) and POCl3 (2690 g, 17.5 mol) at 80° C. under N2, was slowly added DMF (1584 mL, 20.46 mol) at a rate such that the temperature remained between 80-90° C. After stirring for 16 hr at 85° C., the dark solution was poured cautiously onto 7 Kg of ice. (Quench required 1.5 hr due to violent exotherm) The mixture was extracted twice with EtOAc (total volume 16 L). The combined EtOAc layers were washed once with aq. NaHCO3 and then with brine. Upon concentration, 881 g of 4-formyl-2-isopropylanisole was obtained.

Workup

  1. customat 80° C.
  2. customremained between 80-90° C
  3. custom(Quench required 1.5 hr due to violent exotherm) The mixture
  4. extractionwas extracted twice with EtOAc (total volume 16 L)
  5. washThe combined EtOAc layers were washed once with aq. NaHCO3
  6. concentrationUpon concentration

Sources & evidence

ORD record
ord-969c0fa1948f472890223d6e0ba46a8e
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

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