1,1'-(Diazomethylene)bis(benzene) → HCID 19591445, compound

HRID 849382Notes

Reaction equation

HRID 849382 reaction equation
[C:1]([CH2:4][C:5]1[CH:6]=[C:7]([C:14]([OH:16])=[O:15])[C:8](=[CH:12][CH:13]=1)[C:9]([OH:11])=[O:10])([OH:3])=[O:2].[C:17]1([C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N+]=[N-])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[C:17]1([CH:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:15][C:14]([C:7]2[CH:6]=[C:5]([CH2:4][C:1]([OH:3])=[O:2])[CH:13]=[CH:12][C:8]=2[C:9]([O:11][CH:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:10])=[O:16])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 17881135HCID 17881135, compound

Product 1

HCID 19591445HCID 19591445, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

0.52 g of 4-carboxymethylphthalic acid was dissolved in 10 ml of acetone, and a solution of 0.89 g of diphenyldiazomethane in acetone (20 ml) was dropwise added over a period of 15 minutes at room temperature with stirring. After completion of the dropwise addition, the mixture was stirred at room temperature overnight. Then, the solvent was distilled off, and then, the residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1→ethyl acetate) to obtain 0.67 g of the above identified compound as a colorless oily substance.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringthe mixture was stirred at room temperature overnight
  3. distillationThen, the solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1→ethyl acetate)
  5. customto obtain 0.67 g of the

Sources & evidence

ORD record
ord-40851d0be5854848b9d0c81f766228f9
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

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