Hydrochloric Acid → HCID 20379388, compound

HRID 1415492Notes

Reaction equation

HRID 1415492 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([F:63])([F:62])[C:12]([F:61])([F:60])[O:13][C:14]([F:59])([F:58])[C:15]([F:57])([F:56])[O:16][C:17]([F:55])([F:54])[C:18]([F:53])([F:52])[O:19][C:20]([F:51])([F:50])[C:21]([F:49])([F:48])[C:22]([F:47])([F:46])[C:23]([F:45])([F:44])[C:24]([F:43])([F:42])[O:25][C:26]([F:41])([F:40])[C:27]([F:39])([F:38])[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([N+:35]([O-])=O)[CH:29]=2)[CH:7]=[CH:8][C:9]=1[OH:10])([O-])=O.Cl>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:11]([F:62])([F:63])[C:12]([F:60])([F:61])[O:13][C:14]([F:58])([F:59])[C:15]([F:56])([F:57])[O:16][C:17]([F:54])([F:55])[C:18]([F:52])([F:53])[O:19][C:20]([F:50])([F:51])[C:21]([F:48])([F:49])[C:22]([F:46])([F:47])[C:23]([F:44])([F:45])[C:24]([F:42])([F:43])[O:25][C:26]([F:41])([F:40])[C:27]([F:39])([F:38])[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([NH2:35])[CH:29]=2)[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21482461HCID 21482461, compound

Product 1

HCID 20379388HCID 20379388, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1,17-Bis(3-nitro-4-hydroxyphenyl)perfluoro-3,6,9,15-tetraoxaheptadecane (3.00 g, 0.0030 mole) was dissolved in 180 ml of methanol and the solution deoxygenated by passing nitrogen through the boiling solution for 15 minutes. Concentrated hydrochloric acid (20 ml, 0.23 mole) and 10% Pd/C (0.30 g) were cautiously added to the cooled solution and catalytic reduction to the desired product took place over night at 50 psi of hydrogen. The catalyst was filtered off and the clear white solution evaporated to dryness under reduced pressure to yield the slightly off-white dihydrochloride salt. It was stirred vigorously in a water-ether mixture which was treated carefully with solid sodium bicarbonate. The ether layer was washed several times with water, dried over magnesium sulfate and evaporated to dryness. The residue was recrystallized twice from approximately 1400 ml of heptane (charcoal) to yield 1.41 g (50% yield) of slightly off-white product (VIII), m.p. 92°-95° C.

Workup

  1. customthe solution deoxygenated
  2. customfor 15 minutes

Sources & evidence

ORD record
ord-c4ceb1f2c1bb4e9a972f5188cd5a63c3
Source dataset
uspto-grants-1977_01
Patent number
US04005142

Reaction notes

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