Hydrochloric Acid → HCID 54454409, compound

HRID 1076793Notes

Reaction equation

HRID 1076793 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]([CH2:11][CH3:12])[C:8](Cl)=[O:9])=[CH:4][CH:3]=1.[C:15]1(=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[CH2:16]1.N1CCCCC1.Cl>N1C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]([CH2:11][CH3:12])[C:8]([CH:16]2[C:15](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:24])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 118151,3-IndandioneHCID 13239464HCID 13239464, compound

Product 1

HCID 54454409HCID 54454409, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

5.8 G of 2-(4-chlorophenoxy)butyryl chloride (0.025 mol) are added dropwise, with stirring and whilst cooling with an ice bath at 0°C and working under nitrogen, to 3.65 g (0.025 mol) of indane-1,3-dione in 20 ml of pyridine containing two drops of piperidine. After stirring the mixture for 18 hours, it is poured onto ice and acidified with hydrochloric acid, and the resulting mixture is ectracted with chloroform. After evaporating the solvent, the residue is crystallised from ethyl acetate to give 1.55 g of pure 2-[2'-(4"-chlorophenoxy)butyryl]indane-1,3-dione, melting point 132°C. Empirical formula: C19H15O4Cl; molecular Weight: 342.79; Elementary analysis:

Workup

  1. stirringAfter stirring the mixture for 18 hours
  2. additionit is poured onto ice
  3. customAfter evaporating the solvent
  4. customthe residue is crystallised from ethyl acetate

Sources & evidence

ORD record
ord-2164147d246642959df2b2a011079141
Source dataset
uspto-grants-1976_05
Patent number
US03957879

Reaction notes

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