Pyridine → HCID 19761580, compound

HRID 249372Notes

Reaction equation

HRID 249372 reaction equation
[OH:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH2:12])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].N1C=CC=CC=1.[C:19](Cl)(=[O:21])[CH3:20]>ClCCl>[C:19]([O:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[CH2:12])=[CH:9][CH:10]=1)([CH3:4])[CH3:3])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 12542438Benzenemethanol, 4-ethenyl-α,α-dimethyl-

Product 1

HCID 19761580HCID 19761580, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 6.7 g of 1-(1-hydroxy-1-methylethyl)-4-ethenyl-benzene and 4.0 g of pyridine in 100 ml of dichloromethane was stirred while 4.0 g of acetyl chloride in 20 ml of dichloromethane was added dropwise. After the addition was complete, the mixture was refluxed gently overnight. After cooling, an additional 30 ml of dichloromethane was added and the mixture was then washed with 50 ml of cold 5% aqueous HCl, and then several times with 30 ml portions of water. After drying over magnesium sulfate, filtering, and concentrating, the crude product was purified by HPLC using ethyl/acetate hexane as eluent. This method affords 4.05 g (47.5% yield) of the desired compound.

Workup

  1. additionwas added dropwise
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed gently overnight
  4. temperatureAfter cooling
  5. washthe mixture was then washed with 50 ml of cold 5% aqueous HCl
  6. dry with materialAfter drying over magnesium sulfate
  7. filtrationfiltering
  8. concentrationconcentrating
  9. customthe crude product was purified by HPLC

Sources & evidence

ORD record
ord-019f8082bdd04ef4abf35da904ff1c8e
Source dataset
uspto-grants-1993_05
Patent number
US05214105

Reaction notes

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