1-Iodopropane → HCID 54011623, compound

HRID 1074107Notes

Reaction equation

HRID 1074107 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C@@H:2]([CH3:4])[OH:3].I[CH2:9][CH2:10][CH3:11]>[Ag]=O.CCOCC>[CH2:9]([O:3][C@H:2]([CH3:4])[C:1]([O:6][CH3:7])=[O:5])[CH2:10][CH3:11]

Participants

5

Procedure

Silver oxide (87.5 g, 0.38 mol) was added to a mixture of (R)-methyl lactate (52.1 g, 0.5 mol) with 1-iodopropane (100 g, 0.59 mol) over 3 hours, followed by allowing the mixture to stand at room temperature for 4 days, adding ether (200 ml) for dilution, filtering the mixture, distilling off ether, washing the residue with 2N-NaOH aqueous solution, drying over anhydrous sodium sulfate, distilling it under reduced pressure to obtain (R)-methyl 2-propoxypropionate (46.1 g, b.p. 33°-34° C./5 mmHg). To this (R)-methyl 2-propoxypropionate (28.2 g) were added water (60 ml) and NaOH (10 g), followed by agitating the mixture at room temperature for 3 hours, pouring the mixture in 6N-hydrochloric acid (80 ml), extracting the resulting organic layer with ether, washing the resulting organic layer with water and distilling off ether to obtain 2-propoxypropionic acid (18.0 g).

Workup

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

Sources & evidence

ORD record
ord-392f8453d7a14d2a8353866ec40a7332
Source dataset
uspto-grants-1990_11
Patent number
US04973426

Reaction notes

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