Butyl iodide → HCID 54574557, compound

HRID 1106043Notes

Reaction equation

HRID 1106043 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[CH:10]([CH3:23])[CH2:11][CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[CH2:26](I)[CH2:27][CH2:28][CH3:29]>C(O)C>[CH2:1]([O:8][C:9](=[O:24])[CH:10]([CH3:23])[CH2:11][C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:26][CH2:27][CH2:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 5360545SodiumHCID 56613533HCID 56613533, compound

Product 1

HCID 54574557HCID 54574557, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

4,4-Diethoxycarbonyl-2-methylbutyric acid benzyl ester [prepared by Michael condensation of benzylmethacrylate and malonic ester as per J. Am. Chem. Soc., 52, 4598 (1930)] (3.36 g, 10 mmole) is added to a solution of 0.23 g of sodium in ethanol (3 ml) chilled to 10° C. Butyl iodide (1.85 g, 10 mmoles) is added and the mixture is refluxed for four hours. The solvent is removed in vacuo and the mixture is distilled in vacuo to yield 4,4-diethoxycarbonyl-2-methyloctanoic acid benzyl ester.

Workup

  1. temperaturethe mixture is refluxed for four hours
  2. customThe solvent is removed in vacuo
  3. distillationthe mixture is distilled in vacuo

Sources & evidence

ORD record
ord-ad55016d321044abbe27bb093513bf5c
Source dataset
uspto-grants-1982_01
Patent number
US04311705

Reaction notes

Loading…