Hydrochloric Acid → 1-Oxo-indan-4-carboxylic acid

HRID 2377227Notes

Reaction equation

HRID 2377227 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])([OH:3])=O.[Cl-].[Na+].[Cl-].[Al+3].[Cl-].[Cl-].Cl>O>[O:3]=[C:1]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]=2[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 2262943-(2-Carboxyphenyl)propionic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 125422061-Oxo-indan-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-(2-carboxyethyl)benzoic acid (1.0 g, 5.15 mmol), sodium chloride (320 mg, 5.41 mmol) and aluminum chloride (3.43 g, 25.75 mmol) was heated to about 160° C. for about 2 hours. The mixture was cooled with an acetone/dry ice bath and a mixture of ice and water was slowly added, followed by concentrated hydrochloric acid (AMOUNT). The mixture was filtered and the obtained solid was purified by flash chromatography on silica gel using dichloromethane/methanol (50:1) as eluent. The product was further recrystallized from methanol to provide the desired product. MS (ESI): m/z 175 (M−H)−.

Workup

  1. temperatureThe mixture was cooled with an acetone/dry ice bath
  2. additionwas slowly added
  3. filtrationThe mixture was filtered
  4. customthe obtained solid was purified by flash chromatography on silica gel
  5. customThe product was further recrystallized from methanol

Sources & evidence

ORD record
ord-edc2842283164ad0a7bcc13373d7ffef
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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