Butyl iodide → HCID 53885111, compound

HRID 1090029Notes

Reaction equation

HRID 1090029 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C@H:2]([CH3:4])[OH:3].I[CH2:10][CH2:11][CH2:12][CH3:13]>[Ag]=O.CCOCC>[CH2:10]([O:3][C@@H:2]([CH3:4])[C:1]([O:6][CH2:7][CH3:8])=[O:5])[CH2:11][CH2:12][CH3:13]

Participants

5

Procedure

Silver oxide (77.5 g, 0.3 mol) was added to a mixture of ethyl L-(+)-lactate (49.4 g, 0.4 mol) with 1-iodobutane (100 g, 0.5 mol) over 2 hours, followed by allowing the mixture to stand at room temperature for 3 days, adding ether (30 ml) to dilute it, filtering, distilling off ether, washing the residue with 2N-NaOH aqueous solution, drying it over anhydrous magnesium sulfate and distilling it to obtain ethyl (S)-2-butyloxypropionate (30.7 g) (b.p. 64° C./7 mmHg), adding to this product, 5N-NaOH aqueous solution (50 ml), agitating the mixture at room temperature for 5 hours, pouring it in 6N-HCl (75 ml), adding ether, agitating the mixture, washing the resulting organic layer with water and distilling off ether to obtain (S)-2-butyloxypropionic acid (21.4 g).

Workup

  1. additionto dilute it
  2. filtrationfiltering
  3. distillationdistilling off ether
  4. washwashing the residue with 2N-NaOH aqueous solution
  5. dry with materialdrying it over anhydrous magnesium sulfate
  6. distillationdistilling it

Sources & evidence

ORD record
ord-10d228b60e564481ade5e233349807f3
Source dataset
uspto-grants-1992_01
Patent number
US05080827

Reaction notes

Loading…