Sodium Hypochlorite Pentahydrate

Experimental procedure (large-scale synthesis of (diacetoxyiodo)benzene):
Iodobenzene (7.5 mL, 67 mmol) in AcOH (100 mL) is added to a vigorously stirred solid of NaClO·5H₂O (11 g, 70 mmol) in a 1 L beaker at room temperature under air. After 10 min, CH₂Cl₂ (200 mL) and toluene (200 mL) are added, and the separated aqueous phase is removed and filtered. The filtrate is concentrated to a half of its original volume (ca. 50 mL) under reduced pressure to yield a white suspension, which is then added excess hexane (∼ 200 mL) and filtered to give (diacetoxyiodo)benzene (17 g, 79%) as a white solid.

Experimental procedure¹⁾: NaOCl·5H₂O (2.0 g, 12.2 mmol) is added in one portion to a mixture of Bu₄NHSO₄ (0.17 g, 0.50 mmol), TEMPO (21 mg, 0.13 mmol), and 2-octanol (1.30 g, 10.0 mmol) in CH₂Cl₂ (10 mL) at 5 °C. The reaction is stopped after 0.5 h by quenching with aq. sat. Na₂SO₃ solution (20 mL). The organic layer is separated, and the aqueous layer is extracted with CH₂Cl₂ (30 mL). The combined organic layers are washed with H₂O (30 mL), dried over Na₂SO₄, and concentrated to give 2-octanone as colorless oil (1.27 g, 95%).