Hydrochloric Acid → HCID 178466058, compound

HRID 1824632Notes

Reaction equation

HRID 1824632 reaction equation
[C:1]([C-:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)(=[O:3])[CH3:2].[C-:9]1([C:14](=O)[CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10]1.[Fe+2:17].Cl.O>C1(C)C=CC=CC=1>[C:1]([C-:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)(=[O:3])[CH3:2].[CH2:14]([C-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)[CH3:15].[Fe+2:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178466059HCID 178466059, compound

Product 1

HCID 178466058HCID 178466058, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,1′-Diacetylferrocene (5.0 g, 20 mmol) in toluene (20 mL) was added to a freshly prepared mixture of zinc/mercury amalgam (3.0 g of granulated Zn, 0.2 g of HgCl2), 10 M HCl (20 mL) and water (20 mL). The reaction mixture was heated to reflux for 4 h with vigorous stirring. The mixture was cooled to rt and extracted with toluene (3×50 mL) and the organic layer was washed with water (3×100 mL) and satd aq NaHCO3 (3×50 mL). The organic layer was dried (MgSO4), evaporated, and chromatographed (silica, petroleum ether:ether, 1:10) to afford 2.8 g (60%) of a red-brown oil. 1H NMR δ 1.13 (t, J=7.5 Hz, 3H), 2.26 (q, J=7.5 Hz, 2H), 2.36 (s, 3H), 4.08 (s, 4H), 4.44 (t, J=2.1 Hz, 2H), 4.69 (t, J=2.1 Hz, 2H); 13C NMR δ 15.4, 22.2, 28.2, 69.8, 69.9, 70.7, 73.6, 92.5, 202.8; FAB-MS obsd 256.0544, calcd exact mass 256.0551 (C14H16FeO). Spectral and physical properties concur with published data (Rosenblum et al. (1958) J. Am. Chem. Soc., 80: 5443–5448).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 h with vigorous stirring
  3. extractionextracted with toluene (3×50 mL)
  4. washthe organic layer was washed with water (3×100 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated
  7. customchromatographed (silica, petroleum ether:ether, 1:10)

Sources & evidence

ORD record
ord-85b845cb3f4446469656e41169eeaabe
Source dataset
uspto-grants-2006_05
Patent number
US07042755B1

Reaction notes

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