Epichlorohydrin → HCID 19020730, compound

HRID 1109522Notes

Reaction equation

HRID 1109522 reaction equation
[OH:1][C:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4][N:3]=1.[CH2:14]([CH:16]1[O:18][CH2:17]1)[Cl:15]>>[Cl:15][CH2:14][CH:16]([OH:18])[CH2:17][N:3]1[C:2](=[O:1])[C:6]([CH3:7])=[C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:4]1

Participants

3

Reactant 2

HCID 7835EpichlorohydrinHCID 178431794HCID 178431794, compound

Product 1

HCID 19020730HCID 19020730, compoundYield 71.1%

Conditions

Temperature
75 °C

Procedure

A mixture of 6.00 g (34.2 mmoles) of 3-hydroxy-4-methyl-5-phenylisoxazole and 6.33 g (68.4 mmoles) of epichlorohydrin was stirred, whilst heating at 75° C., for 5 hours. At the end of this time, the excess epichlorohydrin was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 2:1 by volume mixture of cyclohexane and ethyl acetate as eluent, to give 6.51 g (yield 71.1%) of the title compound as a colorless powder, melting at 82°-83° C.

Workup

  1. customAt the end of this time, the excess epichlorohydrin was removed by distillation under reduced pressure
  2. customthe resulting residue was purified by column chromatography through silica gel
  3. additionby volume mixture of cyclohexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-4a99420139df4f55b2a7ae76e6a3e80e
Source dataset
uspto-grants-1994_06
Patent number
US05321037

Reaction notes

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