Butyl iodide → HCID 53885111, compound

HRID 1074105Notes

Reaction equation

HRID 1074105 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 (S)-(+)-ethyl 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) for dilution, filtering the resulting mixture, distilling off ether, washing the residue with 2N-NaOH aqueous solution, drying it over anhydrous MgSO4 and distilling under reduced pressure, to obtain (S)-ethyl 2-butoxypropionate (30.7 g, b.p. 64° C./7 mmHg), adding thereto 5N-NaOH aqueous solution (50 ml), agitating the mixture at room temperature for 5 hours, pouring it in 6N-hydrochloric acid (75 ml) to extract the resulting organic layer with ether, washing the resulting organic layer with water and distilling off ether, to obtain (S)-2-butoxypropionic acid (21. 4 g).

Workup

  1. filtrationfiltering the resulting mixture
  2. distillationdistilling off ether
  3. washwashing the residue with 2N-NaOH aqueous solution
  4. dry with materialdrying it over anhydrous MgSO4
  5. distillationdistilling under reduced pressure

Sources & evidence

ORD record
ord-efc2d6d7ecd64d04ba7fa467e678e87a
Source dataset
uspto-grants-1990_11
Patent number
US04973426

Reaction notes

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