1,3-Benzodioxole-4-carboxaldehyde → 1,3-Dioxaindane-4-carboxylic acid

HRID 1837143Notes

Reaction equation

HRID 1837143 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]1[O:24][C:23]2[C:16](=[C:17]([CH:20]=[CH:21][CH:22]=2)[CH:18]=[O:19])[O:15]1>CC(C)=O>[CH2:14]1[O:24][C:23]2[C:16](=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]([OH:3])=[O:19])[O:15]1

Participants

4

Reactant 2

HCID 822641,3-Benzodioxole-4-carboxaldehydeHCID 131709961Jones' reagent

Product 1

HCID 3048321,3-Dioxaindane-4-carboxylic acidYield 1,805.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Freshly prepared Jones reagent (0.2 mmol) was added dropwise (until a brown color persisted in the reaction) to a solution of 2-methylenedioxybenzaldehyde (1.0 g, 6.67 mmol) in 10 mL of acetone at 0° C. The reaction was completed after 4 hours at 0° C., and it was poured onto ethyl ether (20 mL). The ether solution was then washed with brine and extracted with 1N NaOH solution. The NaOH extract was acidified with concentration HCl, and product was extracted out with ether (3×10 mL). Ether layers were combined, dried, and evaporated to give 0.6 g pure product; this compound was used for the next step without further purification (54%). M+167.0

Workup

  1. additionit was poured onto ethyl ether (20 mL)
  2. washThe ether solution was then washed with brine
  3. extractionextracted with 1N NaOH solution
  4. extractionThe NaOH extract
  5. concentrationwas acidified with concentration HCl, and product
  6. extractionwas extracted out with ether (3×10 mL)
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-143bf0c621bd481ba1e24f772f1df5e4
Source dataset
uspto-grants-2004_08
Patent number
US06780883B2

Reaction notes

Loading…