Pyridine → HCID 3614560, compound

HRID 1356708Notes

Reaction equation

HRID 1356708 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][CH:7]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:8][CH2:9][OH:10].N1C=CC=CC=1>ClCCl>[Cl:1][CH2:2][C:3]([O:10][CH2:9][CH2:8][CH:7]([CH3:6])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 108312Phenylisohexanol

Product 1

HCID 3614560HCID 3614560, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 127.05 g (1.125 mol) of chloroacetyl chloride and 200 ml of dichloromethane were out into a flask and, while stirring under ice-cooling, a mixture consisting of 199.6 g (1.12 mol) of 3-methyl-5-phenylpentanol and 88.59 g (1.12mol) of pyridine was added dropwise thereto spending 2 hours (reaction temperature 5 to 15° C.). After completion of the dropwise addition, this was further stirred at room temperature for 3 hours, and white crystals of the thus precipitated pyridine hydrochloride were removed by filtration. The reaction mixture was washed with water (3×300 ml), the organic phase was dehydrated with anhydrous magnesium sulfate and then the solvent was evaporated under a reduced pressure. By distilling the remained yellow oil under a reduced pressure, the title compound was obtained as a light yellow transparent oil. Yield 242.25 g (0.849 mol; yield 84.9%, boiling point 148-151° C./0.2 kPa).

Workup

  1. temperaturecooling
  2. additionwas added dropwise
  3. custom(reaction temperature 5 to 15° C.)
  4. additionAfter completion of the dropwise addition
  5. stirringthis was further stirred at room temperature for 3 hours
  6. customwhite crystals of the thus precipitated pyridine hydrochloride were removed by filtration
  7. washThe reaction mixture was washed with water (3×300 ml)
  8. customthe solvent was evaporated under a reduced pressure
  9. distillationBy distilling the remained yellow oil under a reduced pressure

Sources & evidence

ORD record
ord-ff860837d3fe4808941a8d6bc54d78b3
Source dataset
uspto-grants-2003_07
Patent number
US06586639B2

Reaction notes

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