Hydrochloric Acid → HCID 20082008, compound

HRID 1464296Notes

Reaction equation

HRID 1464296 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([C:8]2[CH:9]=[C:10]([C:17]([OH:19])=[O:18])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])=[O:7])=[CH:4][CH:3]=1.CCOCC.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([Mg]Br)=[CH:30][CH:29]=1.Cl>O1CCCC1.C(OCC)(=O)C>[OH:7][C:6]([C:31]1[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=1)([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:21][CH:20]=1)[C:8]1[CH:9]=[C:10]([C:17]([OH:19])=[O:18])[C:11](=[CH:15][CH:16]=1)[C:12]([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 200819974-(4-Chlorobenzoyl)phthalic acidHCID 178478191HCID 178478191, compound

Product 1

HCID 20082008HCID 20082008, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.00 g of 4-(4-chlorobenzoyl) phthalic acid in 63 ml of tetrahydrofuran was dropwise added 50 ml of ether solution (0.59M) of 4-chlorophenylmagnesium bromide at room temperature in 20 minutes. The reaction mixture was refluxed under heating for 3 hours, cooled with ice, hydrolyzed with 10% hydrochloric acid and shaken with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was chromatographed on a column of silica gel, eluting with chloroform and methanol (2:1) to give crude 4-[hydroxybis (4-chlorophenyl) methyl]phthalic acid. This intermediate was provided for the following reaction without further purification.

Workup

  1. customat room temperature
  2. customin 20 minutes
  3. temperatureThe reaction mixture was refluxed
  4. temperatureunder heating for 3 hours
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was chromatographed on a column of silica gel
  9. washeluting with chloroform and methanol (2:1)

Sources & evidence

ORD record
ord-8ae54230ec0e429fafcc1c1abeb6184a
Source dataset
uspto-grants-1994_04
Patent number
US05304556

Reaction notes

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