Epichlorohydrin → 2-[(2-Iodophenoxy)methyl]oxirane

HRID 1906510Notes

Reaction equation

HRID 1906510 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl>>[I:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][CH:13]1[CH2:14][O:15]1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 107842-IodophenolHCID 24758Sodium hydride

Product 1

HCID 130640342-[(2-Iodophenoxy)methyl]oxiraneYield 80%

Conditions

Temperature
70 °C

Procedure

To a round bottom flask under N2 was added 4.56 g (0.095 mole) of 50% NaH in oil. The NaH was washed twice with hexane, then 220 ml of DMF was added. Aliquots of 20.0 g (0.091 mole) of o-iodophenol were added over 15 minutes then 30.0 ml (0.450 mole) of epichlorohydrin was added and the solution heated to 70° C. After two hours the reaction was evaporated in vacuo, taken into CHCl3, washed with 10% NaOH, water, and brine and dried with MgSO4. The solvent was evaporated in vacuo to give 24.93 g of crude product. Distillation at 110°-114° C., 0.05 mm Hg gave 20.0 g (80.0%) of [(2-iodophenoxy)methyl]oxirane.

Workup

  1. washThe NaH was washed twice with hexane
  2. addition220 ml of DMF was added
  3. customAfter two hours the reaction was evaporated in vacuo
  4. washwashed with 10% NaOH, water, and brine
  5. dry with materialdried with MgSO4
  6. customThe solvent was evaporated in vacuo
  7. customto give 24.93 g of crude product
  8. distillationDistillation at 110°-114° C.

Sources & evidence

ORD record
ord-061404c5f26b45a4beaa0c447ab4a4b3
Source dataset
uspto-grants-1987_03
Patent number
US04652584

Reaction notes

Loading…