Pyridine → HCID 18461419, compound

HRID 2303843Notes

Reaction equation

HRID 2303843 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[C:5]([CH3:10])=[CH:4][C:3]=1[OH:11].N1C=CC=CC=1.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>ClCCl>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[C:5]([CH3:10])=[CH:4][C:3]=1[O:11][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 18461306HCID 18461306, compound

Product 1

HCID 18461419HCID 18461419, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 5.91 g of 2-chloro-3,5-dimethylbenzene-1,4-diol, 8.13 g of pyridine and 30 ml of dichloromethane, 10 ml of a dichloromethane solution containing 4.54 g of pivaloyl chloride were added dropwise under ice cooling, followed by stirring at the same temperature for one hour and at room temperature for 90 minutes. The reaction mixture was concentrated by evaporation. Water was added to the concentrate and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=10/1), whereby 8.02 g of the title compound were obtained.

Workup

  1. additionwere added dropwise under ice cooling
  2. concentrationThe reaction mixture was concentrated by evaporation
  3. additionWater was added to the
  4. concentrationconcentrate
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-ded68c4428f34c48a76de7edc4b18438
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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