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

HRID 893717Notes

Reaction equation

HRID 893717 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 (1.7 M, 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-e2081413985048ec9602e8660633e0a5
Source dataset
uspto-grants-1992_06
Patent number
US05126364

Reaction notes

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