Phthalic Anhydride → HCID 58175527, compound

HRID 1945362Notes

Reaction equation

HRID 1945362 reaction equation
[CH3:1][C:2]1([CH3:15])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[C:16]1(=[O:26])[O:21][C:19](=[O:20])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[CH3:1][C:2]1([CH3:15])[C:3]2[CH:4]=[C:5]([C:16]([C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[C:19]([OH:21])=[O:20])=[O:26])[CH:6]=[CH:7][C:8]=2[C:9]2[C:14]1=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 783259,9-DimethylfluoreneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 58175527HCID 58175527, compoundYield 119.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9,9-Dimethyl-9H-fluorene (40 g, 1 eq, 0.146 mol) and phthalic anhydride (36.5 g, 1.1 eq, 0.161 mol) were placed in a reaction vessel, and dichloromethane (1.5 l) was added thereto. Then, aluminum chloride (29.2 g, 1.5 eq, 0.219 mol) was gradually added at 0° C., and the reaction mixture was stirred at room temperature for 12 hours. After the reaction was terminated, distilled water was gradually added at 0° C., and the resultant solution was extracted with an excess of dichloromethane and several times washed with distilled water. After solvent removal, the resultant solid was placed in a hexane (2 l)-containing vessel, washed, filtered, and dried to give 2-(9,9-dimethyl-9H-fluorene-2-carbonyl)benzoic acid (59.8 g, yield=82%).

Workup

  1. customAfter the reaction was terminated
  2. distillationdistilled water
  3. additionwas gradually added at 0° C.
  4. extractionthe resultant solution was extracted with an excess of dichloromethane and several times
  5. washwashed with distilled water
  6. customAfter solvent removal
  7. addition)-containing vessel
  8. washwashed
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-9847b1729f2d4d4fa189b35e2f9cac7a
Source dataset
uspto-grants-2013_03
Patent number
US08395144B2

Reaction notes

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