Hydrochloric Acid → 4-Fluoro-7-hydroxy-2,3-dihydro-1H-inden-1-one

HRID 440831Notes

Reaction equation

HRID 440831 reaction equation
C([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)(=O)C=C.[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+].Cl>>[F:12][C:9]1[CH:8]=[CH:7][C:6]([OH:5])=[C:11]2[C:10]=1[CH2:8][CH2:7][C:6]2=[O:5]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 6451240Aluminum(III) ChlorideHCID 185460004-Fluorophenyl 2-propenoate

Product 1

HCID 152684884-Fluoro-7-hydroxy-2,3-dihydro-1H-inden-1-oneYield 95.8%

Conditions

Temperature
80 °C

Procedure

4-Fluorophenyl acrylate (12.0 g) was added to a mixture of aluminum chloride (33.7 g) and sodium chloride (14.8 g), and the mixture was stirred at 80° C. for 2 hours and then at 160° C. for 1 hour. After completion of the reaction, ice-water and concentrated hydrochloric acid were added, and the reaction mixture was extracted with chloroform. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography. From the eluate of hexane-ethyl acetate (9:1), 4-fluoro-7-hydroxy-1-indanone (5.75 g) was obtained as a pale yellow powder.

Workup

  1. waitat 160° C. for 1 hour
  2. additionwere added
  3. extractionthe reaction mixture was extracted with chloroform
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-61a38ba01aad4f818533352c8b900a7b
Source dataset
uspto-grants-1996_05
Patent number
US05521180

Reaction notes

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