Dimethylformamide → 5-Chloro-2,3-dimethoxybenzaldehyde

HRID 2426090Notes

Reaction equation

HRID 2426090 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:13]N(C=O)C.C(=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([O:10][CH3:13])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 51510865-Chloro-2-hydroxy-3-methoxybenzaldehyde

Product 1

HCID 41722755-Chloro-2,3-dimethoxybenzaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
61 °C

Procedure

A mixture of 5-Chloro-2-hydroxy-3-methoxybenzaldehyde (275 g, 1.47 mol) and DMF were stirred as potassium carbonate (411 g, 2.97 mol) was added over 5 minutes. The mixture temperature rose from 22 to 29° C. over 10 minutes. Dimethylsulfate (283 g, 2.24 mol) was added over 15 minutes causing a temperature rise from 28 to 47° C. The mixture was then heated with a heating mantle to 61° C. over 15 minutes and stirred at 61° C. for 1.5 hours; the reaction was complete by TLC. The reaction mixture was cooled to 22° C., transferred to a 22-L flask and diluted with water (8.2 L) over 5 minutes; the temperature rose to 38° C. The light yellow mixture was filtered and the flask and filter cake rinsed with 1.5 L water. The solid was dried under vacuum for 15 hour at 50° C. The material contained inorganic salts and was suspended in water (3 L) for 1.5 hours. After filtration and a 500 mL water rinse, the filter cake was dried under by suction and overnight at 65° C. under vacuum. Yield: 305 g (100% yield, 99.1% purity).

Workup

  1. additionwas added over 5 minutes
  2. customfrom 28 to 47° C
  3. temperatureThe reaction mixture was cooled to 22° C.
  4. customtransferred to a 22-L flask
  5. customrose to 38° C
  6. filtrationThe light yellow mixture was filtered
  7. filtrationthe flask and filter cake
  8. washrinsed with 1.5 L water
  9. customThe solid was dried under vacuum for 15 hour at 50° C
  10. waitwas suspended in water (3 L) for 1.5 hours
  11. filtrationAfter filtration
  12. washa 500 mL water rinse
  13. customthe filter cake was dried under by suction and overnight at 65° C. under vacuum

Sources & evidence

ORD record
ord-230beaed8f8b4ed3850c19c56fa6e000
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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