From Organikum 15th edition:
WARNING: Thiophenols have a very strong, lasting, terrible, smell, and they can cause severe skin problems. All manipulation of these compounds should be carried out inside a good fume hood, or in a specialy designed laboratory room. All glassware should be handled with rubber gloves and, after the reaction, washed with a KMnO4 solution.
General technique for the preparation of thiophenols:
In a 3 neck 250ml round bottom flask, equiped with a reflux condenser, stirrer and addition funnel, are heated to reflux, under strong agitation, 50ml of glacial acetic acid, 12,5g of red P and 0,6g I2. 0,15 mol of the sulphonyl chloride are slowly added, so as to make the reaction start, wich is evident by the appearance of I2 vapours(solid sulphonyl chlorides are introduced through the condenser). The heat source in then removed, and the addition of the sulphonyl chloride is regulated so as to mantain the boiling of the reaction mixture, taking care that the reaction doesn´t get so violent as to let I2 escape from the top of the condenser. After all as benn added, the mixture is refluxed for two hours, 9ml of water are added and the reflux is mantained for another hour. The products are isolated with a steam distillation.
In the case of liquid Thiophenols the distilate is placed in a sep funnel, the organic layer separated, and the aqueous fase extracted with chloroform. The pooled organic phases are dried with Na2SO4 and the thiophenol is vacuum distilled, after solvent distilation. Solid thiophenols are vaccum filtered and recrystalized from MeOh/water.
Yields range from 50 to 85%, on a variety of substituted benzeneshulphonyl chlorides(aliphatic side chains, phenol ethers and halogenides).
Refs:
Chem Ber. 99, 375(1966)
Z. Chem 10, 449(1970)