Hydrochloric Acid → HCID 15398356, compound

HRID 1824635Notes

Reaction equation

HRID 1824635 reaction equation
N[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[CH-:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1.[Fe+2:25]>O.C1(C)C=CC=CC=1>[C-:15]1([C:2]2[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=2)[CH:19]=[CH:18][CH:17]=[CH:16]1.[CH-:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1.[Fe+2:25].[C-:15]1([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH:19]=[CH:18][CH:17]=[CH:16]1.[CH-:6]1[CH:5]=[CH:8][CH:9]=[CH:2]1.[Fe+2:25]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7611Bis(eta-cyclopentadienyl) ironHCID 693314-Aminobenzyl alcoholHCID 23668193Sodium Nitrite

Product 2

HCID 15398356HCID 15398356, compoundYield 45%HCID 131725737HCID 131725737, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

4-Aminobenzyl alcohol (3.0 g, 24 mmol) was suspended in a mixture of conc. HCl (20 mL) and H2O (20 mL) and cooled to 0° C. under stirring. A solution of NaNO2 (2.1 g, 30 mmol) in H2O (10 mL) was added dropwise while the temperature was carefully maintained between 0–5° C. The resulting mixture was stirred for 30 min at 0° C., then slowly added at 0° C. to a solution of ferrocene (3.7 g, 20 mmol) in toluene (100 mL), resulting in gas evolution. After complete addition, the reaction mixture was stirred at 0° C. for 6 h and warmed to rt. Stirring was continued for another 6 h. The layers were separated and the aqueous layer was extracted with toluene (3×100 mL). The combined organic layers were washed with satd aq NaHCO3 (3×100 mL), brine (3×100 mL), dried (MgSO4) and filtered. The solvent was removed under reduced pressure and the resulting residue was purified by column chromatography (silica, petroleum ether/diethyl ether, 10:2) to afford 0.94 g (20%) of 4-ferrocenylbenzyl alcohol 16 (as well as 2.1 g (45%) of 4-ferrocenylbenzaldehyde 17).

Workup

  1. temperaturewas carefully maintained between 0–5° C
  2. stirringThe resulting mixture was stirred for 30 min at 0° C.
  3. customresulting in gas evolution
  4. additionAfter complete addition
  5. stirringthe reaction mixture was stirred at 0° C. for 6 h
  6. temperaturewarmed to rt
  7. stirringStirring
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted with toluene (3×100 mL)
  10. washThe combined organic layers were washed with satd aq NaHCO3 (3×100 mL), brine (3×100 mL)
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. customThe solvent was removed under reduced pressure
  14. customthe resulting residue was purified by column chromatography (silica, petroleum ether/diethyl ether, 10:2)

Sources & evidence

ORD record
ord-212235f92c9b4ade9889ad9fe3bd18cf
Source dataset
uspto-grants-2006_05
Patent number
US07042755B1

Reaction notes

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