Thionyl Chloride → Butyl 4-(chlorocarbonyl)phenyl carbonate

HRID 411942Notes

Reaction equation

HRID 411942 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:9][C:10]([O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)=[O:11])[CH2:6][CH2:7][CH3:8]>C(Cl)(Cl)(Cl)Cl>[CH2:5]([O:9][C:10]([O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([Cl:3])=[O:18])=[CH:15][CH:14]=1)=[O:11])[CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 586595Butyl 4-Carboxyphenyl Carbonate

Product 1

HCID 71444173Butyl 4-(chlorocarbonyl)phenyl carbonate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

On the other hand, 15 ml of carbon tetrachloride (solvent) and 3 ml of thionyl chloride were added to 2.16 g (0.0158 mol) of 4-n-butoxycarbonyloxy benzoic acid, and the mixture was heated and refluxed. After sufficiently reacting them, excess thionyl chloride and carbon tetrachloride (solvent) were distilled off under reduced pressure to obtain 4-butoxycarbonyloxy benzoic acid chloride (one having Formula 7 wherein R2 is a n-butyl group).

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed
  3. distillationwere distilled off under reduced pressure

Sources & evidence

ORD record
ord-24167b69d65f41989b7f9164bc6f1850
Source dataset
uspto-grants-2003_05
Patent number
US06562259B1

Reaction notes

Loading…