Reaktion #1552018

Reaktionsgleichung

2-naphthalenecarbonyl chloride

pyridine

Ethylene glycol

→

2-naphthoic acid 2-hydroxyethyl ester

Ausbeute 75.8%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas dropped over an hour
2. 2
   workup.STIRRINGThis solution was stirred for 2 hours
3. 3
   workup.STIRRINGsubsequently further stirred at room temperature for 6 hours
4. 4
   SonstigeThe resultant reaction solution
5. 5
   Waschenwas rinsed with water
6. 6
   Sonstigethe organic phase was then separated
7. 7
   Trocknendried over magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled off
9. 9
   SonstigeThe residue was purified by silica gel column chromatography with a methylene chloride/methanol (97/3) solvent mixture

Vorschrift

Ethylene glycol (15.6 g, 252 mmol) was dissolved in 100 mL of methylene chloride. To this solution, 3.49 g (44 mmol) of pyridine was added and the solution was cooled with ice water. To this solution being stirred, a solution containing 8.00 g (42 mmol) of 2-naphthalenecarbonyl chloride dissolved in 80 mL of methylene chloride was dropped over an hour. This solution was stirred for 2 hours and subsequently further stirred at room temperature for 6 hours. The resultant reaction solution was rinsed with water; the organic phase was then separated and dried over magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography with a methylene chloride/methanol (97/3) solvent mixture serving as an eluent to provide 6.88 g of 2-naphthoic acid 2-hydroxyethyl ester.

Quelle