4-Nitrophenol → 2-((4-Nitrophenoxy)methyl)oxirane

HRID 1792764Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([CH:19]1[O:21][CH2:20]1)Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:17][CH:19]2[O:21][CH2:20]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 100 °C

Procedure

1-(4-Nitrophenoxy)-2,3-epoxypropane was prepared by an analogous method to that described by Zhen-Zhong Lui et. al. in Synthetic Communications (1994), 24, 833–838. 4-Nitrophenol (4.0 g), anhydrous potassium carbonate (8.0 g) and tetrabutylammonium bromide (0.4 g) were mixed with epibromohydrin (10 ml). The reaction mixture was heated at 100° C. for 1 hour. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate and filtered. The filtrate was evaporated to dryness and the residue was codistilled twice with toluene. The resulting oil was purified by column chromatography and eluted with ethanol (1.0%):dichloromethane to yield on evaporation an oil that crystallised (4.36 g, 77.7% yield). NMR (CDCl3): 2.78 (m, 1H), 2.95 (m, 1H), 3.38 (m, 1H), 4.02 (dd, 1H), 4.38 (dd, 1H), 7.00 (d, 2H), 8.20 (d, 2H); m/z 196 [MH]+.

Workup

temperatureAfter cooling to ambient temperature
filtrationfiltered
customThe filtrate was evaporated to dryness
customThe resulting oil was purified by column chromatography
washeluted with ethanol (1.0%)
customdichloromethane to yield on evaporation an oil that
customcrystallised (4.36 g, 77.7% yield)

Sources & evidence

ORD record: ord-1dcb26f6d6184ee3b17c092fca446c72
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07078410B2

Reaction notes

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