Hydrochloric Acid → 6-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid

HRID 19554

Reaction equation

HRID 19554 reaction equation
C[O:2][C:3]([C:5]1[C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][CH:10]=[C:9]([OH:20])[CH:8]=2)=[O:4].CSC.B(Br)(Br)Br.C(=O)(O)[O-].[Na+].Cl>ClC(Cl)C>[OH:20][C:9]1[CH:8]=[C:7]2[C:12]([C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:5]([C:3]([OH:4])=[O:2])[C:6]2=[O:21])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10946916Boron tribromide methyl sulfideHCID 687002636-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid methyl ester

Product 1

HCID 686989826-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acidYield 48.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid methyl ester (2.6 g, 9.28 mmol) obtained in Step 1 was dissolved in dichloroethane, and boron tribromide methyl sulfide (6.0 mL, 27.84 mmol) was added thereto. The mixture was refluxed for 2 hrs at 90° C., cooled in an ice bath, neutralized using sodium bicarbonate, and adjusted to pH 2 using 6N hydrochloric acid. The resulting mixture washed successively with dichloromethane and water. The organic layer was separated, dried over anhydrous MgSO4, concentrated under a reduced pressure and recrystallized to obtain 1.2 g of the titled compound (yield: 48.6%).

Workup

  1. temperaturecooled in an ice bath
  2. washThe resulting mixture washed successively with dichloromethane and water
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customrecrystallized

Sources & evidence

ORD record
ord-df3eb7c1c5c742609cdcc4e6d4b8dcbe
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Linked notes

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