Sodium Chloride → Methyl 1-methoxy-2-naphthoate

HRID 1381922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1381922
[OH-].[K+].[OH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[C:14]([OH:16])=O.[CH3:17]I.[Cl-].[Na+].CN(C)[CH:23]=[O:24]>>[CH3:17][O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[C:14]([O:24][CH3:23])=[O:16]

Komponenten

6

Edukt 5

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 68441-Hydroxy-2-naphthoic acidHCID 14797Potassium Hydroxide

Produkt 1

HCID 4640332Methyl 1-methoxy-2-naphthoate

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Over a 15 minute period, 149 g. (2.7 moles) of ground potassium hydroxide is added to 180 g. (0.96 mole) of 1-hydroxy-2-naphthoic acid in 2.5 l. of dimethylformamide (during the course of which the temperature rises to 32° C.). The reaction mixture is stirred at 20°-25° C. for 16 hours and at 50° C. for 2 hours and cooled to 40° C. 387 g. (2.7 moles) of methyl iodide is added, and the reaction mixture is stirred at 40°-50° C. for 4 hours. 4 l. of saturated sodium chloride solution is added, and the mixture is extracted with diethyl ether. The diethyl ether extract is dried over anhydrous sodium sulfate and evaporated at reduced pressure to obtain the crude product as a light brown oil (255 g.).

Aufarbeitung

  1. customrises to 32° C.
  2. temperaturecooled to 40° C
  3. stirringthe reaction mixture is stirred at 40°-50° C. for 4 hours
  4. extractionthe mixture is extracted with diethyl ether
  5. extractionThe diethyl ether extract
  6. dry with materialis dried over anhydrous sodium sulfate
  7. customevaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f40011dfb59f48c3bc68df255addbf3b
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04804679

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