Butyl iodide → HCID 13668406, compound

HRID 1638953Notes

Reaction equation

HRID 1638953 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]>CCOCC>[CH2:7]([O:6][C:1](=[O:5])[CH:2]([O:3][CH2:10][CH2:11][CH2:12][CH3:13])[CH3:4])[CH3:8]

Participants

4

Reactant 2

HCID 10962Butyl iodideHCID 92831(L)-ethyl lactate

Product 1

HCID 13668406HCID 13668406, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

31.5 g of ethyl L-(+)-lactate and 107.3 g of 1-iodobutane were mixed into a four-necked flask, and freshly synthesized Ag2O was added in 2 hours. After left standing at room temperature for 15 hours, the mixture was diluted with 200 ml of ether, filtered and then ether was evaporated. The residue was washed with 100 ml of an aqueous 5% KOH, dried over anhydrous Na2SO4 and subjected to vacuum distillation. The fractions at 110° C./54 mmHg were collected to give 23 g of (-)-ethyl-2-butoxypropionate. Optical rotation [α]d24° =-73°

Workup

  1. additionfreshly synthesized Ag2O was added in 2 hours
  2. filtrationfiltered
  3. customether was evaporated
  4. washThe residue was washed with 100 ml of an aqueous 5% KOH
  5. dry with materialdried over anhydrous Na2SO4
  6. distillationsubjected to vacuum distillation
  7. customThe fractions at 110° C./54 mmHg were collected

Sources & evidence

ORD record
ord-03ab2ef91d2b4e68958c300999786f0d
Source dataset
uspto-grants-1989_11
Patent number
US04882085

Reaction notes

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