Pyrophosphoric acid → HCID 178519397, compound

HRID 1195464Notes

Reaction equation

HRID 1195464 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.P(OP(O)(O)=O)(O)(O)=O.[CH-:25]1[CH:29]=[CH:28][CH:27]=[CH:26]1.[CH-:30]1[CH:34]=[CH:33][CH:32]=[CH:31]1.[Fe+2:35].[OH-:36].[Na+].[CH2:38]([Cl:40])Cl>O.C(N(CC)CC)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[C-:10]([C:9]([C-:25]3[CH:29]=[CH:28][CH:27]=[C:26]3[C:33]3[CH:32]=[CH:31][C:38]([Cl:40])=[CH:30][CH:34]=3)=[O:36])[CH:2]=[CH:3][CH:4]=2)=[CH:4][CH:3]=1.[CH-:6]1[CH:5]=[CH:9][CH:10]=[CH:2]1.[Fe+2:35].[CH-:6]1[CH:5]=[CH:9][CH:10]=[CH:2]1.[Fe+2:35]

Participants

9

Reactant 6

HCID 1023Pyrophosphoric acidHCID 63184-Chlorobenzoic AcidHCID 6344DichloromethaneHCID 7611Bis(eta-cyclopentadienyl) ironHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride

Product 1

HCID 178519397HCID 178519397, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

5.30 of p-chlorobenzoic acid, 1.0 ml of triethylamine, and 2 ml of phosphorus oxychloride were added and stirred at 0° C. for 30 minutes with 40 ml of methylene chloride, and 60 ml of pyrophosphoric acid and 6.0 g of ferrocene were added. The resulting mixture was heat-refluxed, then poured into water, and made to be basic with sodium hydroxide, subjected to extraction with methylene chloride, and dried. Subsequently, the unreacted ferrocene was removed with column chromatography, to obtain 6.16 g of p-chlorophenylferrocenyl ketone represented by the formula (E), in a yield of 61.0%. The proton nuclear magnetic resonance (1H--NMR) spectrum of the product is shown in FIG. 5. The result showed that the resulting product was the desired compound (p-chlorophenylferrocenyl ketone). ##STR12##

Workup

  1. additionwere added
  2. temperatureThe resulting mixture was heat-refluxed
  3. extractionsubjected to extraction with methylene chloride
  4. customdried
  5. customSubsequently, the unreacted ferrocene was removed with column chromatography

Sources & evidence

ORD record
ord-976b4655ebe048f498607ff4b39a97f3
Source dataset
uspto-grants-1992_05
Patent number
US05110964

Reaction notes

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