Water → (7-Nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol

HRID 1242904Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18]([CH:20]1[O:22][CH2:21]1)Br.O>CN(C)C=O.C(OCC)(=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]2[O:1][CH2:18][CH:20]([CH2:21][OH:22])[O:11][C:3]=2[CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

1,2-Dihydroxy-4-nitrobenzene (5.00 g, 0.032 mol), potassium carbonate (9.67 g, 0.07 mol) and epibromohydrin (5.30 g. 0.039 mol) were dissolved in dimethylformamide (100 ml), which was stirred at 100° C. for 1 hour. Water was added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was washed with water, and concentrated. The residue was purified by alumina column chromatography (development solvent: ethyl acetate). The eluent was washed with a mixed solution of ethyl acetate-n-hexane (1:1), to give (7-nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol (3.31 g) as a white powder.

Workup

washThe organic layer was washed with water
concentrationconcentrated
customThe residue was purified by alumina column chromatography (development solvent: ethyl acetate)
washThe eluent was washed with a mixed solution of ethyl acetate-n-hexane (1:1)

Sources & evidence

ORD record: ord-1423a2f621584dfc847740a8d98a504a
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115750B1

Reaction notes

Loading…