1-Iodododecane → HCID 14793560, compound

HRID 1196434Notes

Reaction equation

HRID 1196434 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][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CCOCC>[CH2:7]([O:6][C:1](=[O:5])[CH:2]([O:3][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10])[CH3:4])[CH3:8]

Participants

4

Reactant 2

HCID 202821-IodododecaneHCID 92831(L)-ethyl lactate

Product 1

HCID 14793560HCID 14793560, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

47.0 g of ethyl L-(+)-lactate and 88.4 g of 1-iodododecane were added into a flask and mixed under nitrogen gas stream. 42.1 g of freshly synthesized Ag2O was added in 3 hours. After the mixture was left standing at room temperature for 50 hours, it was heated on a water bath at 60°-70° C. for 4 hours. The mixture was diluted with 200 ml of ether, subjected to filtration and then ether was evaporated. The residue was washed with 100 ml of aqueous 5% KOH, then dried over anhydrous Na2SO4 and subjected to vacuum distillation. The fractions of 169° C./9 mmHg were collected to obtain 22 g of (-)-ethyl-2-dodecyloxypropionate. Optical rotation [α]D23° =-42°.

Workup

  1. additionmixed under nitrogen gas stream
  2. addition42.1 g of freshly synthesized Ag2O was added in 3 hours
  3. waitAfter the mixture was left
  4. temperatureit was heated on a water bath at 60°-70° C. for 4 hours
  5. filtrationsubjected to filtration
  6. customether was evaporated
  7. washThe residue was washed with 100 ml of aqueous 5% KOH
  8. dry with materialdried over anhydrous Na2SO4
  9. distillationsubjected to vacuum distillation
  10. customThe fractions of 169° C./9 mmHg were collected

Sources & evidence

ORD record
ord-2806341fa31041ae91874be904f71915
Source dataset
uspto-grants-1992_05
Patent number
US05114613

Reaction notes

Loading…