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

HRID 2287613Notes

Reaction equation

HRID 2287613 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-74a33d3cfd504163a5322ad5a8952fa4
Source dataset
uspto-grants-2000_07
Patent number
US06084057

Reaction notes

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