Dimethylformamide → HCID 10798398, compound

HRID 1003354Notes

Reaction equation

HRID 1003354 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1O)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].CI.[C:16](=O)([O-])[O-].[K+].[K+].CN([CH:25]=[O:26])C>>[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:26][CH3:25])[C:7]([O:9][CH3:16])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 91792453-Acetyl-4-hydroxybenzoic acid

Product 1

HCID 10798398HCID 10798398, compound

Procedure

3-Acetyl-4-hydroxybenzoic acid (3.60 g, 20 mmol) and methyl iodide (5.68 g, 40 mmol) were dissolved in 60 ml of DMF, followed by the addition of 11.06 g (80 mmol) of potassium carbonate. The resulting mixture was stirred at room temperature for 2 hours. The DMF was distilled off under reduced pressure, followed by the addition of water. The resulting mixture was extracted with chloroform. The organic layer was dried over MgSO4, the solvent was distilled off under reduced pressure, and the residue was recrystallized from acetone-hexane, whereby 1.42 g of the title compound were obtained as brown powder (yield: 34%).

Workup

  1. distillationThe DMF was distilled off under reduced pressure
  2. additionfollowed by the addition of water
  3. extractionThe resulting mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried over MgSO4
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-0babf8cb5bcb46ebbe683ced8c096fac
Source dataset
uspto-grants-2000_04
Patent number
US06046212

Reaction notes

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