Reaktion #54514

Reaktionsgleichung

tetrahydrofuran

acetyl chloride

tetrahydrofuran

5-chloro-2-dodecyl-3-hydroxy-1,4-naphthoquinone

tetrahydrofuran

sodium hydride

tetrahydrofuran

→

3-acetoxy-5-chloro-2-dodecyl-1,4-naphthoquinone

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter 45 minutes of stirring
2. 2
   workup.STIRRINGthe mixture stirred for 5 hours
3. 3
   Waschenwashed with water, 10% hydrochloric acid, four more times with water
4. 4
   Trocknendried over sodium sulfate
5. 5
   SonstigeThe resulting yellow solid was purified by column chromatography on silica gel
6. 6
   SonstigeSolvent removal

Vorschrift

A solution of 0.95 parts of 5-chloro-2-dodecyl-3-hydroxy-1,4-naphthoquinone in 20 parts of anhydrous tetrahydrofuran was added under nitrogen to a mixture of 0.0635 parts of dispersed sodium hydride in 40 parts of tetrahydrofuran with stirring at room temperature. After 45 minutes of stirring, a solution of 0.275 parts of acetyl chloride in 30 parts of tetrahydrofuran was added and the mixture stirred for 5 hours. The tetrahydrofuran was stripped under reduced pressure and the residue taken up in methylene chloride and then washed with water, 10% hydrochloric acid, four more times with water, dried over sodium sulfate and stripped. The resulting yellow solid was purified by column chromatography on silica gel using 1-chlorobutane as eluent. Solvent removal gave 0.9 parts of 3-acetoxy-5-chloro-2-dodecyl-1,4-naphthoquinone, m.p. 57°-59° C.

Quelle