Pyridine → 5-Methyl-2-(propan-2-yl)cyclohexyl 2-chloroacetate

HRID 492134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 492134
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH:6]1([CH3:16])[CH2:11][CH2:10][CH:9]([CH:12]([CH3:14])[CH3:13])[CH:8]([OH:15])[CH2:7]1.N1C=CC=CC=1>C(OCC)C>[Cl:1][CH2:2][C:3]([O:15][CH:8]1[CH:9]([CH:12]([CH3:13])[CH3:14])[CH2:10][CH2:11][CH:6]([CH3:16])[CH2:7]1)=[O:4]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 1254MentholHCID 6577Chloroacetyl chloride

Produkt 1

HCID 27701965-Methyl-2-(propan-2-yl)cyclohexyl 2-chloroacetateAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of chloroacetyl chloride (6.4 mL, 80 mmol) in 40 mL anhydrous diethyl ether was added dropwise within 2 h to a solution of (−)-menthol (3a) (12.5 g, 80 mmol) and pyridine (6.5 mL, 80 mmol) in anhydrous diethyl ether (160 mL) at 0° C. After warming to RT, the white suspension was stirred for 2 h and the resulting mixture was then filtered. The filtrate was washed with HCl (60 mL, 2 N), saturated. NaHCO3 (60 mL), brine and dried with Na2SO4. Removal of the solvent and drying under vacuum afford (−)-menthyl chloroacetate (4a) (17.64 g, 94%), which was used without further purification. U.S. Pat. No. 4,456,611; Helv. Chim. Acta 1988, 71, 1553.

Aufarbeitung

  1. filtrationthe resulting mixture was then filtered
  2. washThe filtrate was washed with HCl (60 mL, 2 N)
  3. dry with materialNaHCO3 (60 mL), brine and dried with Na2SO4
  4. customRemoval of the solvent
  5. customdrying under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e3590352aee84ee898f6d72a0f1c25af
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531662B2

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