Epichlorohydrin → 3-Methyl-4-[(oxiran-2-yl)methoxy]-1,2-benzoxazole

HRID 2083207Notes

Reaction equation

HRID 2083207 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[C:8]2[C:9]([OH:13])=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][N:5]=1.[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl>CO>[CH3:3][C:4]1[C:8]2[C:9]([O:13][CH2:14][CH:16]3[O:18][CH2:17]3)=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][N:5]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 1354299403-Methyl-1,2-benzoxazol-4-ol

Product 1

HCID 197882843-Methyl-4-[(oxiran-2-yl)methoxy]-1,2-benzoxazoleYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

. . . . To a solution of sodium hydroxide (0.7 g, 17 mmole) in methanol (40 ml) is gradually added 3-methyl-4-hydroxy-1,2-benzisoxazole (15 mmole) and then epichlorohydrin (20 ml). The mixture is stirred at room temperature for 18 hours. After evaporation of methanol and excess epichlorohydrin under reduced pressure, the residue is extracted with chloroform. The extract is washed with a dilute solution of sodium hydroxide and water, dried over magnesium sulfate, and evaporated. The residue is subjected to column chromatography using silica gel and eluted with chloroform. The solvent is evaporated. The residue is recrystallized from isopropyl ether to give 3-methyl-4-(2,3-epoxypropoxy)-1,2-benzisoxazole as colorless prisms melting at 51°-53° C (yield 95.0%).

Workup

  1. customAfter evaporation of methanol and excess epichlorohydrin under reduced pressure
  2. extractionthe residue is extracted with chloroform
  3. washThe extract is washed with a dilute solution of sodium hydroxide and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. washeluted with chloroform
  7. customThe solvent is evaporated
  8. customThe residue is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-ea4d660ad947469291d415d2f28dc5d7
Source dataset
uspto-grants-1978_04
Patent number
US04085114

Reaction notes

Loading…