Phenyl phenylmethyl carbonate

Colorless to clear yellow liquid

This compound is a known compound, but it is not commercially available. It was prepared by following a published procedure. (Rich et al., J. Org. Chem., 1978, 43, 3624). To a mixture of benzyl alcohol (freshly distilled, 69.2 g, 0.64 mol), pyridine (64 mL) and CHAccording to: Pittelkow, M.; Lewinsky, R.; and Christensen, J. B. Synthesis 2002, 15, 2195- 2202.Phenyl chloroformate (54.1 g, 500 mmol) was added dropwise to a mixture of benzyl alcohol (78.3 g, 500 mmol), dichloromethane (90 ml) and pyridine (50 ml) in a 1 l-f lask with condenser and addition funnel. The mixture was stirred for 1 h. Water (125 ml) was added. The phases were separated. The organic phase was washed with dilute sulfuric acid (2 M, 2x125 ml). Brine had to be added in the final wash in order to obtain good separation. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude compound was vacuum destilled to yield a colourless liquid. Yield:104.3 g, 91 percent EPO Benzyl phenyl carbonateAccording to: Pittelkow, M.; Lewinsky, R.; and Christensen, J. B. Synthesis 2002, 15, 2195- 2202.Phenyl chloroformate (54.1 g, 500 mmol) was added dropwise to a mixture of benzyl alcohol (78.3 g, 500 mmol), dichloromethane (90 ml) and pyridine (50 ml) in a 1 l-f lask with condenser and addition funnel. The mixture was stirred for 1 h. Water (125 ml) was added. EPO General procedure: The alcohol, thiol, or amine starting material (1.0 equiv.) was combined with the phenyl chloroformate reagent (1.0 equiv.) in anhydrous CHSynthesis of benzyl phenyl carbonate (Synthesis, 2002, 15, 2195-2202) General procedure: All the reactions were carried out in a 16 mL stainless-steelautoclave with stirring at 600 rpm and equipped with an automatic stirrer and temperature control system. In a typicalreaction procedure, IL (0.60 mmol, 1.2 equiv.), benzyl bromide(0.5 mmol, 85.5 mg, 1.0 equiv.), and alcohols (1.0 mmol, 2.0equiv.) were added into the autoclave successively. CO2 (1.0MPa) was charged into the reactor at room temperature. The autoclave was stirred at 25°C for an appropriate time. Afterreaction, the excess of CO2 was vented. Ethyl ether (2 mL) was added to the mixture, and the crude product was extracted intothe ether layer. The pure product was obtained after evaporation of solvent and excess starting materials.

Molecular Weight:228.24
XLogP3:3.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:228.078644241
Monoisotopic Mass:228.078644241
Topological Polar Surface Area:35.5
Heavy Atom Count:17
Complexity:228
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes