Hydrochloric Acid → HCID 21326215, compound

HRID 1764085Notes

Reaction equation

HRID 1764085 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([F:40])([F:39])[C:12]([F:38])([F:37])[O:13][C:14]([F:36])([F:35])[C:15]([F:34])([F:33])[O:16][C:17]([F:32])([F:31])[C:18]([F:30])([F:29])[C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([N+:26]([O-])=O)[CH:20]=2)[CH:7]=[CH:8][C:9]=1[OH:10])([O-])=O.Cl.[H][H]>C(O)C.[Pd]>[NH2:26][C:21]1[CH:20]=[C:19]([C:18]([F:29])([F:30])[C:17]([F:31])([F:32])[O:16][C:15]([F:33])([F:34])[C:14]([F:35])([F:36])[O:13][C:12]([F:37])([F:38])[C:11]([F:40])([F:39])[C:6]2[CH:7]=[CH:8][C:9]([OH:10])=[C:4]([NH2:1])[CH:5]=2)[CH:24]=[CH:23][C:22]=1[OH:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 22770277HCID 22770277, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21326215HCID 21326215, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1,8-bis(3-nitro-4-hydroxyphenyl)perfluoro-3,6-dioxaoctane (6.10 g, 0.010 mole) in 185 ml of ethanol was deoxygenated by passing nitrogen through the boiling solution for 14 minutes. Concentrated hydrochloric acid (37 ml, 0.44 mole) and 10% Pd/C(0.75 g) were added to the cooled solution and the catalytic reduction was run overnight at room temperature and 50 psi of hydrogen. The catalyst was filtered off and the water white solution reduced to dryness under water aspirator pressure. The light tan residue (6.1 g) was slurried in a water-ether mixture. After careful neutralization with solid sodium bicarbonate, the product dissolved in the ether layer, which was washed several times with water, dried over magnesium sulfate and evaporated to dryness. The soluble portion of the filtrate was taken up in 6 liters of boiling heptane, the solution treated with charcoal and reduced in volume to 3 liters to give upon cooling 2.9 g (53% yield) of slightly off-white product, mp 150°-152° C.

Workup

  1. customfor 14 minutes
  2. filtrationThe catalyst was filtered off
  3. dissolutionAfter careful neutralization with solid sodium bicarbonate, the product dissolved in the ether layer, which
  4. washwas washed several times with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. additionthe solution treated with charcoal
  8. customto give
  9. temperatureupon cooling 2.9 g (53% yield) of slightly off-white product, mp 150°-152° C.

Sources & evidence

ORD record
ord-c635f318d96a4234baa4a9f2be35e2f0
Source dataset
uspto-grants-1978_09
Patent number
US04115367

Reaction notes

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