Acetic Acid → 4-(6-Hydroxy-2,2,3,3,4,4,5,5-octafluorohexyloxy)tetrafluoronitrobenzene

HRID 1267556Notes

Reaction equation

HRID 1267556 reaction equation
[F:1][C:2]([F:16])([C:5]([F:15])([F:14])[C:6]([F:13])([F:12])[C:7]([F:11])([F:10])[CH2:8][OH:9])[CH2:3][OH:4].[F:17][C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[C:22]([F:27])[C:21]([F:28])=[C:20](F)[C:19]=1[F:30].C(N(CC)CC)C.C(O)(=O)C>CN1C(=O)CCC1.O>[OH:9][CH2:8][C:7]([F:10])([F:11])[C:6]([F:13])([F:12])[C:5]([F:14])([F:15])[C:2]([F:16])([F:1])[CH2:3][O:4][C:20]1[C:19]([F:30])=[C:18]([F:17])[C:23]([N+:24]([O-:26])=[O:25])=[C:22]([F:27])[C:21]=1[F:28]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 70154PentafluoronitrobenzeneHCID 1361812,2,3,3,4,4,5,5-Octafluorohexane-1,6-diol

Product 1

HCID 185466184-(6-Hydroxy-2,2,3,3,4,4,5,5-octafluorohexyloxy)tetrafluoronitrobenzeneYield 67.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2,2,3,3,4,4,5,5-octafluoro-1,6-hexanediol (7.86 g) was treated with pentafluoronitrobenzene (2.13 g) and triethylamine (1.39 mL) in NMP (15 mL) at room temperature for 1 hr. The mixture was diluted with water, acidified with acetic acid, and extracted with ethyl ether. The extract was washed with water and brine; dried (MgSO4) and concentrated. Excess diol was removed by distillation and the residual oil purified by chromatography to give 4-(6-hydroxy-2,2,3,3,4,4,5,5-octafluorohexyloxy)tetrafluoronitrobenzene (3.06 g).

Workup

  1. extractionextracted with ethyl ether
  2. washThe extract was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customExcess diol was removed by distillation
  6. customthe residual oil purified by chromatography

Sources & evidence

ORD record
ord-3eac74dfdca740b8916ad7cb36dc5d43
Source dataset
uspto-grants-2003_04
Patent number
US06552161B1

Reaction notes

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