Potassium Hydroxide → 4-(6-Hydroxy-2,2,3,3,4,4,5,5-octafluorohexyloxy)-2,3,5,6-tetrafluorobenzeneamine

HRID 1267557Notes

Reaction equation

HRID 1267557 reaction equation
[OH:1][CH2:2][C:3]([F:29])([F:28])[C:4]([F:27])([F:26])[C:5]([F:25])([F:24])[C:6]([F:23])([F:22])[CH2:7][O:8][C:9]1[C:14]([F:15])=[C:13]([F:16])[C:12]([N+:17]([O-])=O)=[C:11]([F:20])[C:10]=1[F:21].O.O.[Sn](Cl)Cl.[OH-].[K+]>C(O)C.O>[OH:1][CH2:2][C:3]([F:28])([F:29])[C:4]([F:27])([F:26])[C:5]([F:24])([F:25])[C:6]([F:22])([F:23])[CH2:7][O:8][C:9]1[C:14]([F:15])=[C:13]([F:16])[C:12]([NH2:17])=[C:11]([F:20])[C:10]=1[F:21]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 61436Stannous chloride dihydrateHCID 185466184-(6-Hydroxy-2,2,3,3,4,4,5,5-octafluorohexyloxy)tetrafluoronitrobenzene

Product 1

HCID 185466114-(6-Hydroxy-2,2,3,3,4,4,5,5-octafluorohexyloxy)-2,3,5,6-tetrafluorobenzeneamineYield 94.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of the 4-(6-hydroxy-2,2,3,3,4,4,5,5-octafluorohexyloxy)-2,3,5,6-tetrafluoronitrobenzene (2.0 g) in ethanol (50 mL) was treated with tin (II) chloride dihydrate (9.9 g) at 60° C. for 18 hrs. under a nitrogen atmosphere. The mixture was diluted with ice water, basified with potassium hydroxide (10.1 g) in water (80 mL) and extracted with ethyl ether. The extracts were washed with water and brine, dried (K2CO3), and concentrated to an oil. The oil was purified by chromatography to give 4-(6-Hydroxy-2,2,3,3,4,4,5,5-octafluorohexyloxy)-2,3,5,6-tetrafluorobenzeneamine as an oil (1.77 g).

Workup

  1. extractionextracted with ethyl ether
  2. washThe extracts were washed with water and brine
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated to an oil
  5. customThe oil was purified by chromatography

Sources & evidence

ORD record
ord-7b407bdc074e404890b5dd8d90312905
Source dataset
uspto-grants-2003_04
Patent number
US06552161B1

Reaction notes

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