Nitromethane → 3,3,3-Trifluoro-1-nitropropene

HRID 711509Notes

Reaction equation

HRID 711509 reaction equation
[F:1][C:2]([F:7])([F:6])[CH:3](O)O.[CH3:8][N+:9]([O-:11])=[O:10].C([O-])([O-])=O.[Na+].[Na+].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O>[F:1][C:2]([F:7])([F:6])[CH:3]=[CH:8][N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 10340Sodium CarbonateHCID 14812Phosphorus oxide (P4O10)HCID 679012,2,2-Trifluoro-1,1-ethanediol

Product 1

HCID 2206333,3,3-Trifluoro-1-nitropropeneYield 10%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,2,2-trifluoroethane-1,1-diol (75% aq solution, 20 g, 0.13 mol), CH3NO2 (24 g, 0.39 mol) and Na2CO3 (0.85 g, 8 mmol) was stirred overnight at RT. Water (50 mL) was added and the mixture was extracted with diethyl ether (3×30 mL) and dried over Na2SO4. After concentrating the organic extract at low temperature and under reduced pressure, P2O5 (20.0 g, 0.14 mol) was added to the residue oil, which was distilled at atmospheric pressure to give a green-yellow oil (4 g, 50% purity, 10% yield). Boiling point 85-90° C.; 1H NMR (400 MHz, CDCl3) δ ppm 7.09-7.17 (m, 1H), 7.50 (dd, J=2.0 Hz, 12.0 Hz, 1H).

Workup

  1. extractionthe mixture was extracted with diethyl ether (3×30 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationAfter concentrating the
  4. additionwas added to the residue oil, which
  5. distillationwas distilled at atmospheric pressure
  6. customto give a green-yellow oil (4 g, 50% purity, 10% yield)

Sources & evidence

ORD record
ord-6ea9210ceed446dcac6ead6e01b1f95a
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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