Pyridine → Cyclohexyl acetate

HRID 2223993Notes

Reaction equation

HRID 2223993 reaction equation
N1C=CC=CC=1.Cl[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[C:15](OC(=O)C)(=[O:17])[CH3:16]>O>[C:15]([O:14][CH:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 748286-Chloro-1-hexanol

Product 1

HCID 12146Cyclohexyl acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, pyridine (934 g) was added to 6-chlorohexanol (800 g). Acetic anhydride (1,200 mL) was added thereto, and after refluxing under heating for 3 hours, the reaction solution was poured into water and extracted with toluene. The organic layer was neutralized with a saturated sodium hydrogencarbonate aqueous solution, and after washing with water, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the concentrated product was purified by distillation under reduced pressure to obtain 6-acetoxycyclohexane (983 g).

Workup

  1. temperatureafter refluxing
  2. temperatureunder heating for 3 hours
  3. extractionextracted with toluene
  4. washafter washing with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. distillationthe concentrated product was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-da90f4b3cad749fbb270241ecb3176da
Source dataset
uspto-grants-2008_05
Patent number
US07378135B2

Reaction notes

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