Benzyltrimethylammonium hydroxide → HCID 370270, compound

HRID 2220681Notes

Reaction equation

HRID 2220681 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([CH2:7][C:8](=[O:17])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[CH:3][CH:2]=1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([C:28]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)=O)=O)=[CH:22][CH:21]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C(O)C>[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([C:7]2[C:8](=[O:17])[C:9]([C:10]3[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=3)=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)[C:26]=2[C:23]2[CH:22]=[CH:21][C:20]([CH3:19])=[CH:25][CH:24]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 66854Benzyltrimethylammonium hydroxideHCID 769961,2-Bis(4-methylphenyl)-1,2-ethanedioneHCID 124202141,3-Bis(4-methylphenyl)propan-2-one

Product 1

HCID 370270HCID 370270, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

23.13 g (0.11 mol) of 1,3-bis(p-tolyl)-2-propanone and 26.2 g (0.11 mol) of 4,4′-dimethylbenzil were dissolved in 75 ml of hot ethanol (abs.). 53 ml of a methanolic benzyltrimethylammonium hydroxide solution (0.11 mol Triton B, 35% Fluka) were slowly added dropwise at 80° C. with stirring (caution: the reaction batch froths vigorously) and refluxing was effected for 25 minutes. The crude product was filtered off after three hours, then washed with cold ethanol and recrystallized from toluene (violet red, yield: 46.2 g (95%); m.p.: 244-245° C., literature: 250.4-251.4° C. [15]; elemental analysis for C33H38O: found: C, 89.8%, H, 6.6%. calculated: C, 89.96%, H, 6.41%, MS-El [m/z (rel. intensity): M+440 (100), 412 (47), 206 (98), 191 (16), 189 (10)). The IR spectrum of 1,2,3,4-tetra(p-tolyl)cyclopenta-1,3-dien-5-one is shown in FIG. 10.

Workup

  1. temperaturethe reaction batch froths vigorously) and refluxing
  2. filtrationThe crude product was filtered off after three hours
  3. washwashed with cold ethanol
  4. customrecrystallized from toluene (violet red, yield: 46.2 g (95%)
  5. custom250.4-251.4° C. [15]

Sources & evidence

ORD record
ord-31efafc87f324f3991366b5227a41a6d
Source dataset
uspto-grants-2008_08
Patent number
US07417247B2

Reaction notes

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