Thiophosgene → HCID 13563671, compound

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[CH:9][C:10]=1[Cl:11])([CH3:4])([CH3:3])[CH3:2].[C:13](Cl)([Cl:15])=[S:14].[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:15][C:13]([O:12][C:7]1[CH:8]=[CH:9][C:10]([Cl:11])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[S:14]

Participants

Procedure

Into 50 ml of chloroform were dissolved 9.2 g of 3-tert-butyl-4-chlorophenol and 6.3 g of thiophosgene, and 60 ml of 1N-sodium hydroxide solution were added dropwise thereto with stirring at room temperature. After completion of this dropwise addition, the mixture was subjected to stirring over a period of 3 hours. From the reaction mixture was separated chloroform layer, which was thereafter dried over anhydrous calcium chloride. Then, chloroform was distilled off and the residue was distilled under reduced pressure to give 9.5 g of O-3-tert-butyl-4-chlorophenyl chlorothioformate having boiling point of 103°-106° C./0.5 mmHg, of which properties are as follows.