o-Fluorobenzaldehyde → 2-(2-Fluorophenyl)-6-nitro-1,3-benzodioxan

HRID 248804Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][OH:5].[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O>C(OCC)(=O)C.C(O)(=O)C1C=CC=CC=1>[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]1[O:1][C:2]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=2[CH2:4][O:5]1

Participants

Conditions

Temperature: 5 °C

Procedure

An intimate mixture of 2-hydroxy-5-nitrobenzyl alcohol (4.56g), 2-fluorobenzaldehyde (4.02g) and benzoic acid (0.2g) was stirred and heated to 90° C. (±5° C.) under nitrogen for 31/2 hours. The resulting clear reaction mixture was left to cool for two days whereupon it solidified. This material was dissolved in ethyl acetate (250 ml) and the solution was washed with saturated aqueous sodium bicarbonate, 20% aqueous sodium bisulphite and then with water. The organic phase was dried over sodium sulphate and evaporated to yield the crude product as a solid residue which was purified by suspending briefly in hot ethanol and cooling to 0°-5° C. The pure product was thus obtained as a white crystalline powder (5.3g, 71%), mp 137°-138° C.

Workup

waitThe resulting clear reaction mixture was left
temperatureto cool for two days whereupon it
washthe solution was washed with saturated aqueous sodium bicarbonate, 20% aqueous sodium bisulphite
dry with materialThe organic phase was dried over sodium sulphate
customevaporated
customto yield the crude product as a solid residue which
customwas purified
temperaturecooling to 0°-5° C

Sources & evidence

ORD record: ord-11223fd4d4f44dee9296bb6f86e70e14
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05212171

Reaction notes

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