Benzyltrimethylammonium hydroxide → HCID 86734504, compound

HRID 596545

Reaction equation

HRID 596545 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=1)=[CH2:2].[OH-:16].C([N+](C)(C)C)C1C=CC=CC=1>N1C=CC=CC=1>[CH:1]([C:3]1[C:4](=[O:16])[C:5]2[C:13](=[CH:14][CH:15]=1)[C:12]1[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH:6]=2)=[CH2:2]

Participants

4

Reactant 2

HCID 66854Benzyltrimethylammonium hydroxideHCID 110416072-ethenyl-9H-fluorene

Product 1

HCID 86734504HCID 86734504, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
0 °C

Procedure

The 2-vinylfluorene prepared in Example I is dissolved in 800 milliliters of pyridine and cooled to 0° C. One-half milliliter of a 40% solution of benzyltrimethyl ammonium hydroxide in pyridine is slowly added with air being bubbled through the reaction solution. The initially formed red coloration fades over a period of 1 to 2 hours and the solution is poured into water and extracted with benzene to yield 9 grams (90% theory) of a yellow solid. The residue is chromatographed on alumina (Woehlm basic) and eluted with benzene. Recrystallization from hexane gives 2-vinylfluorenone as a pale yellow material (melting point 69°-70° C). The structure of the product is confirmed by nuclear magnetic resonance and elemental analysis.

Workup

  1. custombeing bubbled through the reaction solution
  2. additionthe solution is poured into water
  3. extractionextracted with benzene
  4. customto yield 9 grams (90% theory) of a yellow solid
  5. customThe residue is chromatographed on alumina (Woehlm basic)
  6. washeluted with benzene
  7. customRecrystallization from hexane

Sources & evidence

ORD record
ord-5050f0d7c04f41ca9cf04023d55c24f4
Source dataset
uspto-grants-1977_03
Patent number
US04011266

Linked notes

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