Thio (CAS NO.: ), which is also known as Benzoic acid, thio, could be produced through the following synthetic routes.

A solution of 200 g. (3 moles) of potassium hydroxide (85%) pellets in 800 ml. of 90% ethanol is prepared with mechanical stirring in a 2-l. three-necked round-bottomed flask. The flask is fitted with a 500-ml. dropping funnel and a gas inlet tube extending to the bottom of the flask, and hydrogen sulfide is passed in through the inlet tube with stirring and cooling until the solution is saturated and does not give an alkaline reaction with phenolphthalein. The mixture is further cooled to 10–15° by means of an ice bath, and 200 g. (1.41 moles) of freshly distilled benzoyl chloride is introduced drop-wise over a period of about 1.5 hours with stirring while the temperature is kept below 15°. After the addition of the benzoyl chloride has been completed, the reaction mixture is stirred for an additional hour. The potassium chloride which precipitates during the addition is separated quickly by filtration through a Büchner funnel and is washed with about 200 ml. of 95% ethanol. The filtrate is placed in a 2-l. round-bottomed flask fitted with a condenser arranged for distillation and evaporated to dryness under reduced pressure on a steam bath. The solid residue, consisting mainly of potassium thiobenzoate, is dissolved in about 700 ml. of cold water, and the solution is filtered if considerable insoluble material is present. The alkaline solution is extracted with 500 ml. of benzene in order to remove any neutral material. The aqueous layer is then acidified with cold 6N hydrochloric acid and extracted with two 500-ml. portions of peroxide-free ether. The ether layer is washed with several portions of cold water and dried over anhydrous sodium sulfate. The ether is evaporated under reduced pressure on a steam bath, and the residue is fractionated immediately through a short (15–20 cm.) Vigreux column at reduced pressure, dry nitrogen being admitted through the capillary. After a very small fore-run, the yellow-orange thiobenzoic acid distils at 85–87°/10 mm. (95–97°/15 mm.); yield 120–150 g. (61–76%); n_D20  1.6027. Upon refractionation, the light-yellow thiobenzoic acid, as determined by titration with standard base or alcoholic iodine, is about 99.5% pure; n_D20  1.6030.