Pyridine → 1-Chloroethyl Hexyl Carbonate

HRID 745042Notes

Reaction equation

HRID 745042 reaction equation
Cl[C:2]([O:4][CH:5]([Cl:7])[CH3:6])=[O:3].[CH2:8]([OH:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:2](=[O:3])([O:14][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[O:4][CH:5]([Cl:7])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 81031-HexanolHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 135066371-Chloroethyl Hexyl Carbonate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-Chloroethyl chloroformate (10.0 g, 69.9 mmol) and 1-hexanol (6.5 g, 63.6 mmol) were dissolved in chloroform (80 ml) at 0° C. Pyridine (5.5 g, 69.5 mmol) was added dropwise during 17 minutes maintaining the temperature below 10° C. After stirring at room temperature for 20 hours the organic phase was washed three times with 1 normal hydrochloric acid, once with a saturated sodium hydrogen carbonate solution and finally twice with water. The organic solution was dried with magnesium sulfate and the solvent was removed at reduced pressure. The residue (11.6 g) was distilled in vacuo (Bp. 61°-72° C., 3×10-3 mbar). Yield: 9.0 g. 1H-NMR (CDCl3): delta=0.89 (CH2CH3); 1.28-1.40 (CH2CH2CH×2CH3); 1.69 (OCH2CH2); 1.83 (CH3CH); 4.20 (OCH2); 6.43 ppm (CH).

Workup

  1. temperaturemaintaining the temperature below 10° C
  2. washwas washed three times with 1 normal hydrochloric acid
  3. dry with materialThe organic solution was dried with magnesium sulfate
  4. customthe solvent was removed at reduced pressure
  5. distillationThe residue (11.6 g) was distilled in vacuo (Bp. 61°-72° C., 3×10-3 mbar)

Sources & evidence

ORD record
ord-7dc503b0cd6e4260bacfbeb5224413e5
Source dataset
uspto-grants-1996_09
Patent number
US05559266

Reaction notes

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