Cyclohexanol → Ethyl (cyclohexyloxy)acetate

HRID 18810

Reaktionsgleichung

Reaktionsgleichung von HRID 18810
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N-]>ClCCl.CCOCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][O:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:15]

Komponenten

6

Edukt 2

HCID 7966CyclohexanolHCID 12192Ethyl diazoacetate

Produkt 1

HCID 93856Ethyl (cyclohexyloxy)acetateAusbeute 887,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 423677Acetic acid, rhodium salt (4:2)KatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of cyclohexanol (1.0 g, 0.95 mmol) in dichloromethane (30 mL) is added rhodium (II) acetate dimer (44 mg) followed by ethyl diazoacetate (1.14 g, 10.0 mmol). The reaction mixture is stirred at RT for 20 min. The reaction mixture is diluted with Et2O, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 1.57 g of the product 407. 1H NMR (CDCl3) δ 4.23 (q, 2H), 4.10 (s, 2H), 3.33 (m, 1H), 1.93 (m, 2H), 1.74 (m, 2H), 1.54 (m, 1H), 1.4-1.1 (m, 8H)

Aufarbeitung

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 150° C.

Quellen und Nachweise

ORD-Eintrag
ord-1a5b12cd52534597acd79291a1c1607a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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