Pyridine → 3-Methylnonan-3-YL-hexahydrobenzoate

HRID 1863149Notes

Reaction equation

HRID 1863149 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])[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CCCCCC>[CH3:1][C:2]([O:11][C:18](=[O:25])[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 75938Cyclohexanecarbonyl chlorideHCID 894283-Nonanol, 3-methyl-

Product 1

HCID 203921343-Methylnonan-3-YL-hexahydrobenzoate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Conditions

Temperature
5 °C

Procedure

36 G. (0.25 mole) of 3-methylnonan-3-ol, 20 g. of pyridine and 60 ml. of hexane are combined and cooled to 5° C. under agitation. To the resulting solution is added, under agitation over a period of 1 to 2 hours while maintaining the reaction temperature between 5°-15° C. a solution of 37 g. (0.25 mole) hexahydrobenzoyl-chloride dissolved in 60 ml. of hexane. 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. portions 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 solution is added, under agitation over a period of 1 to 2 hours
  2. temperaturewhile maintaining the reaction temperature between 5°-15° C. a solution of 37 g
  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-a2a832de6d4f4380bad6b0f7d34f7091
Source dataset
uspto-grants-1979_09
Patent number
US04168248

Reaction notes

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