Dichloromethane → HCID 58175527, compound

HRID 517305Notes

Reaction equation

HRID 517305 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.ClCCl.[Cl-].[Al+3].[Cl-].[Cl-]>O>[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

6

Reactant 4

HCID 6344DichloromethaneHCID 6811Phthalic AnhydrideHCID 783259,9-DimethylfluoreneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 58175527HCID 58175527, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9,9-dimethyl-9H-fluorene (40 g, 1 eq, 0.206 mol) and Phthalic anhydride (33.6 g, 1.1 eq, 0.227 mol) were placed in a reaction vessel, and added with Dichloromethane (1.5 l). At 0° C., aluminum chloride (40.8 g, 1.5 eq, 0.309 mol) was gradually added thereto, and the temperature was raised up to room temperature. Then, the resultant mixture was stirred for 12 hours. After the reaction was completed, the resultant product was gradually added with distilled water at 0° C. The resultant product was extracted with an excess of dichloromethane, and washed several times with distilled water. After solvent removal, the produced solid was placed in a Hexane 2 l-containing vessel, washed, filtered, and dried, 2-(9,9-dimethyl-9H-fluorene-2-carbonyl)benzoic acid (56.4 g, yield 82%) was obtained.

Workup

  1. extractionThe resultant product was extracted with an excess of dichloromethane
  2. washwashed several times with distilled water
  3. customAfter solvent removal
  4. additioncontaining vessel
  5. washwashed
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-1e6ed23a45b04bf597723c694a9498a6
Source dataset
uspto-grants-2015_08
Patent number
US09115112B2

Reaction notes

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