Carbon Dioxide → 2,3-Dihydro-1-benzofuran-7-carboxylic acid

HRID 1681862Notes

Reaction equation

HRID 1681862 reaction equation
[Li]CCCC.CN(C)CCN(C)C.[O:14]1[CH2:18][CH2:17][C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]1=2.[C:23](=[O:25])=[O:24]>CCCCCC.O>[O:14]1[CH2:18][CH2:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:22]([C:23]([OH:25])=[O:24])[C:15]1=2

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 10329DihydrobenzofuranHCID 178418339Butyllithium

Product 1

HCID 27950142,3-Dihydro-1-benzofuran-7-carboxylic acidYield 54.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent2×

Procedure

To a solution of n-BuLi (1.7M, 123 ml, 0.21 mol) in 400 ml of hexane at room temperature was added 24.3 g (0.21 mol) of N,N,N',N'-tetramethylethylenediamine (TMEDA), followed by a hexane (40 ml) solution of 2,3-dihydrobenzo[b]furan (14) (12.56 g, 0.11 mol). The mixture was stirred under argon at room temperature for 4 hours, and then poured into dry ice (pre-washing with anhydrous ether). After stirring at ambient temperature overnight, the mixture was diluted with water (300 ml), and the layers separated. The aqueous layer was acidified with conc. HCl to pH 1, cooled and the precipitate collected on a filter. This was recrystallized from CH2Cl2 to give 15a (9.43 g, 54.7%) as a white solid, mp 167°-169.5° C.

Workup

  1. stirringAfter stirring at ambient temperature overnight
  2. customthe layers separated
  3. temperaturecooled
  4. customthe precipitate collected on a filter
  5. customThis was recrystallized from CH2Cl2

Sources & evidence

ORD record
ord-c86ad1be55f64faa9e56ba602f5ba1d7
Source dataset
uspto-grants-1992_12
Patent number
US05175173

Reaction notes

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