Pyridine → 3-Methylnonan-3-YL-benzoate

HRID 1863146Notes

Reaction equation

HRID 1863146 reaction equation
[CH3:1][C:2]([OH:11])([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH3:4].N1C=CC=CC=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]([O:11][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 894283-Nonanol, 3-methyl-

Product 1

HCID 203921353-Methylnonan-3-YL-benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
5 °C

Procedure

40.0 G. (0.25 mole) of 3-methylnonan-3-ol, 20. g. of pyridine and 60 ml. of toluene are combined and cooled to 5° C. under agitation. To the resulting solutin is added, under agitation, over a period of 1 to 2 hours while maintaining the reaction temperature between 5°-15° C., a solution of 35.15 g. (0.25 mole) of benzoyl chloride, dissolved in 30 ml. of toluene. The source of cooling is removed and the reaction mixture is agitated overnight, permitting the temperature of the reaction mixture to rise to room temperature (25°-30° C.). After completion of the reaction, the formed pyridine hydrochloride is removed by successive washings with 100 ml. of warm water. The solvent is removed by distillation and the desired ester is rectified by fractional distillation in a vacuum, preferably at 1 mm.

Workup

  1. additionTo the resulting solutin is added, under agitation, over a period of 1 to 2 hours
  2. temperaturewhile maintaining the reaction temperature between 5°-15° C.
  3. temperatureThe source of cooling
  4. customis removed
  5. customto rise to room temperature
  6. custom(25°-30° C.)
  7. customAfter completion of the reaction
  8. customthe formed pyridine hydrochloride is removed by successive washings with 100 ml
  9. customThe solvent is removed by distillation
  10. distillationthe desired ester is rectified by fractional distillation in a vacuum, preferably at 1 mm

Sources & evidence

ORD record
ord-4f33228a264d4b45b05956e1b9951530
Source dataset
uspto-grants-1979_09
Patent number
US04168248

Reaction notes

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