Indene → HCID 21714964, compound

HRID 650303Notes

Reaction equation

HRID 650303 reaction equation
C(N(CC)CC)C.[CH2:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1.[C:17]([C:20]1[CH:21]=[C:22](I)[CH:23]=[CH:24][CH:25]=1)([OH:19])=[O:18]>CC([O-])=O.CC([O-])=O.[Pd+2].C(O)C>[C:17]([C:20]1[CH:21]=[CH:22][C:23]([C:9]2[CH2:10][C:11]3[C:16]([CH:8]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:24][CH:25]=1)([OH:19])=[O:18]

Participants

6

Reactant 3

HCID 7219IndeneHCID 8471TriethylamineHCID 120603-Iodobenzoic acid

Product 1

HCID 21714964HCID 21714964, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolvent

Procedure

20 ml of triethylamine, 2.2 g (20 mmole) of indene, 4.96 g (20 mmole) of meta-carboxy iodo-benzene and 0.134 g (0.6 mmole) of Pd(OAc)2 were stirred under reflux for 10 h. After that the mixture was cooled till room temperature and treated with 100 ml of ethanol. The crystalline precipitate was isolated, and dissolved in aqueous alkali. Aqueous phase was separated and treated with aqueous HCl. White precipitated was isolated washed with cooled ethanol and dried under vacuum to obtain 2 g (43%) of 2-(4-carboxy-phenyl)-indene.

Workup

  1. temperatureunder reflux for 10 h
  2. customThe crystalline precipitate was isolated
  3. dissolutiondissolved in aqueous alkali
  4. customAqueous phase was separated
  5. additiontreated with aqueous HCl
  6. customWhite precipitated
  7. customwas isolated
  8. washwashed with cooled ethanol
  9. customdried under vacuum

Sources & evidence

ORD record
ord-ad21971d19b144289bafb3d9c7b0356b
Source dataset
uspto-grants-2001_08
Patent number
US06271411B1

Reaction notes

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