Carbon Dioxide → 1H-Indene-3-carboxylic acid

HRID 654447Notes

Reaction equation

HRID 654447 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CCCC.[C:14](=[O:16])=[O:15].Cl>C(OCC)C.O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:14]([OH:16])=[O:15])=[CH:2]1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 7219IndeneHCID 7843Butane

Product 1

HCID 842611H-Indene-3-carboxylic acidYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of indene (21.9 mL, 188 mmol) in 150 mL of dry ethyl ether was added 129 mL (200 mmol) of η-BuLi dropwise at room temperature over 30 minutes with the evolution of butane. The rust colored mixture was refluxed for 2 h, and then poured in a thin stream onto 40 g of Dry Ice. The mixture was shaken at room temperature for 2 h, after which time 1 L of H2O was cautiously added. The aqueous layer was acidified with 10% HCl and then extracted with ethyl ether. Recrystallization from benzene gave 20 g (80%) of indene-3-carboxylic acid as yellowish crystals.

Workup

  1. extractionextracted with ethyl ether
  2. customRecrystallization from benzene

Sources & evidence

ORD record
ord-6124f256bb3b44ddba6b14da7e0dcdb8
Source dataset
uspto-grants-1992_07
Patent number
US05132313

Reaction notes

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