Isopropanol → Ethyl isopropoxyacetate

HRID 2053600Notes

Reaction equation

HRID 2053600 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].[N+](=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N-]>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:11]([O:10][C:8](=[O:9])[CH2:7][O:4][CH:2]([CH3:3])[CH3:1])[CH3:12]

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 12192Ethyl diazoacetate

Product 1

HCID 537908Ethyl isopropoxyacetateYield 51.3%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 2-propanol (0.776 mL, 10.0 mmol) in dichloromethane (33 mL) is added rhodium (II) acetate dimer (22 mg) followed by ethyl diazoacetate (1.05 mL, 10.0 mmol). The reaction mixture is stirred at RT for 30 min. The reaction mixture is filtered through celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 750 mg of the product 405. 1H NMR (CDCl3) δ 4.21 (q, 2H), 4.06 (s, 2H), 3.73 (m, 1H), 1.29 (t, 3H), 1.22 (s, 3H), 1.19 (s, 3H); MS: m/z 147 (M++1).

Workup

  1. filtrationThe reaction mixture is filtered through celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 150° C.

Sources & evidence

ORD record
ord-1bf41681088d48eb96d15c187cba6c96
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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