Hydrochloric Acid → 2-Methoxy-4-nitrobenzaldehyde

HRID 2229409Notes

Reaction equation

HRID 2229409 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10](OC(=O)C)[O:11]C(=O)C)=[C:6]([O:19][CH3:20])[CH:5]=1)([O-:3])=[O:2].O1CCOCC1.Cl>O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[C:6]([O:19][CH3:20])[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 115727564-Nitro-2-methoxy-(a,a-bisacetoxy)toluene

Product 1

HCID 27595992-Methoxy-4-nitrobenzaldehydeYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 2 L rounded bottom flask equipped with a condenser and a mechanical stirrer was placed 1A (250.7 g, 0.8851 mol), dioxane (300 mL) and concentrated HCl (60 mL). The reaction mixture was heated to reflux and stirred under N2 for 20 hours. Water (250 mL) was added dropwise while maintaining the reaction mixture at reflux. After cooling to 0° C. with an ice/water bath, the resulting slurry was stirred for 30 minutes and then filtered. The cake was washed with water (4×200 mL) and suction dried for 17 hours to give 4-nitro-2-methoxybenzaldehyde (1B, 146.3 g, 91%) as yellow solid. 1H NMR (CDCl3) d 10.54 (s, 1H), 8.00 (d, J=8.3 Hz, 1H), 7.91 (s, 1H), 7.89 (d, J=8.3 Hz, 1H), 4.08 (s, 3H).

Workup

  1. customTo a 2 L rounded bottom flask equipped with a condenser and a mechanical stirrer
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. temperaturewhile maintaining the reaction mixture
  5. temperatureat reflux
  6. stirringthe resulting slurry was stirred for 30 minutes
  7. filtrationfiltered
  8. washThe cake was washed with water (4×200 mL) and suction
  9. customdried for 17 hours

Sources & evidence

ORD record
ord-9709f0677f6d4c15a414cf343fe57e5b
Source dataset
uspto-grants-2002_07
Patent number
US06420403B1

Reaction notes

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