Pyridine → 1-Chloroethyl Cyclohexyl Carbonate

HRID 892919Notes

Reaction equation

HRID 892919 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 CarbonateYield 88%

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, with stirring, 2.0 ml of 1-chloroethyl chloroformate is added dropwise to the solution over a period of 10 minutes. After completion of addition, the cold bath is removed. 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 (yield 88%) of the title compound as colorless oil.

Workup

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

Sources & evidence

ORD record
ord-786a757287d6453f9a5f753067b78084
Source dataset
uspto-grants-1992_06
Patent number
US05120841

Reaction notes

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