1-Octanol → Octyl 1-chloroethyl carbonate

HRID 1583307Notes

Reaction equation

HRID 1583307 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].N1C=CC=CC=1.Cl[C:17]([O:19][CH:20]([Cl:22])[CH3:21])=[O:18]>CCOCC>[C:17](=[O:18])([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[O:19][CH:20]([Cl:22])[CH3:21]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 1049PyridineHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 13506636Octyl 1-chloroethyl carbonateYield 69.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

To a stirring solution of dry n-octanol (6.42 g, 49.3 mmol) and pyridine (3.90 g, 49.3 mmol) in anhydrous ether (75 mL) was added at 0° C. alpha-chloroethyl chloroformate (prepared according to U.K. Pat. No. 1,426,717; 7.00 g, 49.3 mmol). The mixture was stirred vigorously for three hours at 25° C. then filtered. The filtrate was concentrated in vacuo and distilled at 102°-107° C. (2 mm) affording 8.1 g title product as a clear oil (34.2 mmol, 69.4%): 1H NMR (CDCl3) delta 0.44-2.03 (m, 15H), 1.60 (d, J=6 Hz, 3H), 3.94 (t, J=7 Hz, 2H), 6.18 (q, J=6 Hz, 1H).

Workup

  1. customprepared
  2. filtrationthen filtered
  3. concentrationThe filtrate was concentrated in vacuo
  4. distillationdistilled at 102°-107° C. (2 mm)

Sources & evidence

ORD record
ord-46723b25ac104312b95bd65763b1e852
Source dataset
uspto-grants-1985_11
Patent number
US04551452

Reaction notes

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