Pyridine → 1-Chloroethyl Cyclohexyl Carbonate

HRID 2290199Notes

Reaction equation

HRID 2290199 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.Cl[C:15]([O:17][CH:18]([Cl:20])[CH3:19])=[O:16]>C(Cl)Cl>[C:15](=[O:16])([O:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[O:17][CH:18]([Cl:20])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7966CyclohexanolHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 112295291-Chloroethyl Cyclohexyl Carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.83 g of cyclohexanol and 1.45 g of pyridine in 30 ml of methylene chloride is cooled to -78° C. and 2.0 ml of 1-chloroethyl chloroformate is added dropwise, while stirring, over 10 minutes. Thereafter, the cold bath is removed and the mixture is stirred at room temperature for 16 hours, washed with three 30-ml portions of saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure to give 3.31 g (88% in yield) of the title compound as a colorless oil.

Workup

  1. customThereafter, the cold bath is removed
  2. stirringthe mixture is stirred at room temperature for 16 hours
  3. washwashed with three 30-ml portions of saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent is then distilled off under reduced pressure
  6. customto give

Sources & evidence

ORD record
ord-e94aacf1ecd44f7ebe44fe78d4da61f0
Source dataset
uspto-grants-1986_10
Patent number
US04616008

Reaction notes

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