Potassium Hydroxide → 1,3-Dioxaindane-4-carboxylic acid

HRID 380472

Reaction equation

HRID 380472 reaction equation
[CH2:1]1[O:11][C:10]2[C:3](=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[O:2]1.[OH-:12].[K+]>CCO.O.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]1[O:11][C:10]2[C:3](=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]([OH:12])=[O:6])[O:2]1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 822641,3-Benzodioxole-4-carboxaldehyde

Product 1

HCID 3048321,3-Dioxaindane-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 0.85 g (5.66 mmol) of 2,3-methylenedioxybenzaldehyde (Aldrich) in EtOH at 0° C. was added a solution of 2.12 g (12.45 mmol) of AgNO3 in 7.5 mL of H2O. To this was then added a solution of 1.74 g (31.4 mmol) of KOH in 12 mL of H2O. After 2 h, the reaction mixture was filtered and the filter was washed with EtOH. The filtrate was concentrated and the pH was adjusted to pH=2 to 3 with 6N HCl. The title compound precipitated out and was isolated by filtration to give the title compound. 1H NMR (CDCl3) δ6.16 (s, 2H), 6.92 (t, 1H, J=8 Hz), 7.04 (d, 1H, J=8 Hz), 7.48 (d, 1H, J=8 Hz);

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe filter was washed with EtOH
  3. concentrationThe filtrate was concentrated
  4. customThe title compound precipitated out
  5. customwas isolated by filtration

Sources & evidence

ORD record
ord-c5c6588803d6433d82995a3d76f74d55
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Linked notes

Loading…