2-chloro-5-methoxybenzenethiol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 450 ml of concentrated hydrochloric acid and 1,200 ml of water is added to 157.6 g of 2-chloro-5-methoxy-aniline, while stirring, and the mixture is diazotised with a solution of 69 g of NaNO2 in 130 ml of water at 0°-5°. The mixture is then buffered with sodium acetate and the diazonium salt solution is added dropwise, while stirring, to a solution, at 70°, of 256 g of potassium ethylxanthate in 360 ml of water. After cooling, the mixture is worked up with CH2Cl2 and the resulting crude xanthic acid ester is saponified with KOH in ethanol and the mixture is evaporated, acidified and distilled with steam to give 2-chloro-5-methoxy-thiophenol; b.p. 110°/0.5 mm. After cooling the mixture is evaporated distilled with steam

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 450 ml of concentrated hydrochloric acid and 1,200 ml of water is added to 157.6 g of 2-chloro-5-methoxy-aniline, while stirring, and the mixture is diazotised with a solution of 69 g of NaNO2 in 130 ml of water at 0°-5°. The mixture is then buffered with sodium acetate and the diazonium salt solution is added dropwise, while stirring, to a solution, at 70°, of 256 g of potassium ethylxanthate in 360 ml of water. After cooling, the mixture is worked up with CH2Cl2 and the resulting crude xanthic acid ester is saponified with KOH in ethanol and the mixture is evaporated, acidified and distilled with steam to give 2-chloro-5-methoxy-thiophenol; b.p. 110°/0.5 mm. After cooling the mixture is evaporated distilled with steam