Reaktion #705479

Reaktionsgleichung

4-pentylphenol

pyridine

4-nitrophenyl chloroformate

→

title compound

Ausbeute 28.0%

Carbonic acid (4-nitrophenyl)ester (4-pentylphenyl) ester

Ausbeute 28.0%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   ExtraktionThe reaction was extracted one time with 1N HCl, four times with saturated Na2CO3
3. 3
   Trocknendried (MgSO4)
4. 4
   Sonstigethe solvent removed under reduced pressure
5. 5
   Sonstigeto give 36.97 g of a yellow crytstalline solid
6. 6
   SonstigePurification of the solid on 450 g of silica gel (230-400 mesh)

Vorschrift

A solution of 4-pentylphenol (20.1 g, 0.13 mol) and pyridine (10 ml, 0.13 mol) in 300 ml of methylene chloride was added under nitrogen dropwise over 45 minutes to a solution of 4-nitrophenyl chloroformate (25.28 g, 0.13 mol) in 200 ml of methylene chloride at room temperature. After the addition, the reaction was stirred overnight at room temperature. The reaction was extracted one time with 1N HCl, four times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 36.97 g of a yellow crytstalline solid. Purification of the solid on 450 g of silica gel (230-400 mesh) using 50-60% CH2Cl2 -hexane as the eluent gave 11.58 g (28%) of the title compound as a yellow crystalline solid, mp 67-69° C.

Quelle