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Iron 60 mesh (51.9 g, 0.93 mole), water (220 cc), ethanol (244 cc) and concentrated hydrochloric acid (14.2 cc) were heated to reflux under a nitrogen blanket. Then 2-cyclopentoxynitrobenzene (55.2 g, 0.27 mole) was added at reflux over a period of 2 hrs. The reaction was maintained at reflux for an additional 3 hrs. The pH was adjusted to 7-8 by the addition of concentrated ammonium hydroxide. The reaction mixture then was filtered at 30° C., and the filtrate was washed with 200 cc of ether. The filtrate was extracted with 4×50 cc of ether and the combined ether extracts were subjected to rotary evaporation. The crude product was fractionally distilled at 126°-130° C. at 2.0-2.5 mm. Hg to yield 30.3 g (64.3%) of product.

1. temperatureto reflux under a nitrogen blanket
2. temperatureat reflux over a period of 2 hrs
3. temperatureThe reaction was maintained
4. temperatureat reflux for an additional 3 hrs
5. filtrationThe reaction mixture then was filtered at 30° C.
6. washthe filtrate was washed with 200 cc of ether
7. extractionThe filtrate was extracted with 4×50 cc of ether
8. customthe combined ether extracts were subjected to rotary evaporation
9. distillationThe crude product was fractionally distilled at 126°-130° C. at 2.0-2.5 mm. Hg