Carbon Tetrachloride → 2-Nitro-3-Methylbenzotrichloride

Temperature

47 °C

1 gm of 2-nitro-3-methyl benzyl chloride dissolved in 12 ml of carbon tetrachloride was charged into a reaction vessel with 0.25 gms of tetrabutyl ammonium chloride and 13 ml of methylene chloride. 20 ml of 50% aqueous sodium hydroxide was added to the mixture and the mixture heated for about 31/2 hours at 47° C. After reaction stopped, the organic phase was separated and a fresh charge of aqueous caustic phase with catalyst was added to the organic phase. The mixture was diluted with water, solvent evaporated to give 0.80 gms of crude which was purified by distillation at 110° C. to 120° C. (0.02-0.05 mm/Hg 0.026-0.067×105 pascals) to give a colorless oil which crystallized. Recrystallization from methanol gave colorless crystals. m.p. 61-62° C. Elemental analysis for C8H6Cl3NO2 :

1. customAfter reaction
2. customthe organic phase was separated
3. additiona fresh charge of aqueous caustic phase with catalyst
4. additionwas added to the organic phase
5. additionThe mixture was diluted with water, solvent
6. customevaporated
7. customto give 0.80 gms of crude which
8. distillationwas purified by distillation at 110° C. to 120° C. (0.02-0.05 mm/Hg 0.026-0.067×105 pascals)
9. customto give a colorless oil which
10. customcrystallized
11. customRecrystallization from methanol
12. customgave colorless crystals

ORD record

ord-5a96984bb3094811a13cec05f31f4862

Source dataset

uspto-grants-1986_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04593144