Carbon Dioxide → 1,3-Dioxaindane-4-carboxylic acid

HRID 323054

Reaction equation

HRID 323054 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:2]1.C([Li])CCC.[C:15](=[O:17])=[O:16].C([O-])(O)=O.[Na+]>CCOCC.CCCCCC>[CH2:2]1[O:3][C:4]2[C:5](=[C:6]([C:15]([OH:17])=[O:16])[CH:7]=[CH:8][CH:9]=2)[O:1]1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 92291,3-BenzodioxoleHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 3048321,3-Dioxaindane-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 1,3-benzodioxole (3.09 g, 32 mmol) in dry ether (50 mL) was treated dropwise at −10° C. with 2.5 M n-butyllithium (15 mL, 35 mmol) in hexane. When the addition was complete, the mixture was stirred under reflux for one hour. After cooling to room temperature, it was added to crushed solid carbon dioxide, and after 24 hours, the residue was treated with 10% aq. NaHCO3 and ether. The alkali layer was separated, washed with ether, then acidified with cold concentrated HCl, and extracted with chloroform. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure (1.1 g, 20%). EI-MS m/z 167 (M+H)+

Workup

  1. additionWhen the addition
  2. temperatureunder reflux for one hour
  3. additionit was added
  4. customThe alkali layer was separated
  5. washwashed with ether
  6. extractionextracted with chloroform
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure (1.1 g, 20%)

Sources & evidence

ORD record
ord-6bd0728debdc46e7a3880daac03c840c
Source dataset
uspto-grants-2001_04
Patent number
US06211373B1

Linked notes

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