Benzyl Alcohol → Ethyl 2-(benzyloxy)acetate

HRID 18802

Reaktionsgleichung

Reaktionsgleichung von HRID 18802
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-]>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:16]

Komponenten

5

Edukt 2

HCID 244Benzyl AlcoholHCID 12192Ethyl diazoacetate

Produkt 1

HCID 290299Ethyl 2-(benzyloxy)acetateAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

To a solution of benzyl alcohol (1.04 mL, 10.0 mmol) in dichloromethane (30 mL) is added rhodium (II) acetate dimer (40 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 rotary evaporated, and the residue is vacuum distilled at 110° C. to give 1.81 g of the product 390. 1H NMR (CDCl3) δ 7.4-7.26 (m, 5H), 4.65 (s, 2H), 4.23 (q, 2H), 4.10 (s, 2H), 1.30 (t, 3H).

Aufarbeitung

  1. distillationdistilled at 110° C.

Quellen und Nachweise

ORD-Eintrag
ord-8049abc59b7d4bb6ae237a480e07cebf
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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