Pyridine → Chloromethyl cyclohexyl carbonate

HRID 892918Notes

Reaction equation

HRID 892918 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][CH2:18][Cl: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][CH2:18][Cl:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7966CyclohexanolHCID 62754Chloromethyl chloroformate

Product 1

HCID 13603586Chloromethyl cyclohexyl carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.0 g of cyclohexanol and 2.4 ml of pyridine in 30 ml of methylene chloride is cooled to -78° C. and, with stirring, 2.4 ml of chloromethyl chloroformate is added dropwise to the solution. After completion of addition, a 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 4.5 g of colorless oil, which is crystallized from ligroine giving the title compound as colorless crystals melting at 36°-37° C.

Workup

  1. additionAfter completion of addition, a cold bath
  2. customis 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-f340e814c83e40bdaf92181a5ebbdd2b
Source dataset
uspto-grants-1992_06
Patent number
US05120841

Reaction notes

Loading…