Benzyl Alcohol → Ethyl 2-(benzyloxy)acetate

HRID 2053594Notes

Reaction equation

HRID 2053594 reaction equation
[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]

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 12192Ethyl diazoacetate

Product 1

HCID 290299Ethyl 2-(benzyloxy)acetateYield 93.2%

Reagents, catalysts & solvents 2

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolvent

Procedure

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)

Workup

  1. distillationdistilled at 110° C.

Sources & evidence

ORD record
ord-b6e1dae2633b405ba452c9665a69307e
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

Loading…