Hydrochloric Acid → (1-Oxo-1,3-dihydro-2H-inden-2-ylidene)acetic acid

HRID 232534Notes

Reaction equation

HRID 232534 reaction equation
OS(O)(=O)=O.I([O-])(=O)(=O)=O.[Na+].[C:12]([OH:21])(=[O:20])[CH:13]([CH:15]([C:17]([OH:19])=O)O)O.C1(=O)[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]C1.[OH-].[Na+].Cl>O.C(O)C>[O:19]=[C:17]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][C:15]1=[CH:13][C:12]([OH:21])=[O:20]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8752,3-Dihydroxybutanedioic AcidHCID 1118Sulfuric AcidHCID 67351-IndanoneHCID 14798Sodium HydroxideHCID 23667635Sodium periodate

Product 1

HCID 53400974(1-Oxo-1,3-dihydro-2H-inden-2-ylidene)acetic acidYield 46.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1.3 mL of H2SO4 dissolved in 75 mL H2O was added 11.3 g (0.053 mol) of sodium periodate. The reaction mixture was cooled to 0° C. and 8.0 g (0.053 mol) of tartaric acid was added all at once and stirred for 15 min. at room temperature. 5.0 g (0.038 mol) of 1-indanone was added all at once followed by the dropwise addition of 19.0 g (0.24 mol) of 50% NaOH dissolved in 40 mL of H2O. A white precipitate was formed and 75 mL of ethanol was added. The reaction mixture was stirred at room temperature for 1 hour, acidified to pH ~2 with concentrated HCl and stirred for 18 hours at room temperature, filtered and dried to afford 3.3 g of a yellow solid.

Workup

  1. customA white precipitate was formed
  2. stirringThe reaction mixture was stirred at room temperature for 1 hour
  3. stirringstirred for 18 hours at room temperature
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-a0f0293a206b4ea7bd313c41db1464dd
Source dataset
uspto-grants-1997_01
Patent number
US05591729

Reaction notes

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