Pyridine → HCID 19761580, compound

HRID 1091164Notes

Reaction equation

HRID 1091164 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-77e3af6566764a2581382900c2af2512
Source dataset
uspto-grants-1992_01
Patent number
US05084522

Reaction notes

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