HCID 5249038, compound → HCID 11440186, compound

HRID 2416294Notes

Reaction equation

HRID 2416294 reaction equation
[CH:1]1[C:13]2[C:12]3([C:25]4[CH:24]=[C:23]([CH2:26][OH:27])[CH:22]=[CH:21][C:20]=4[C:19]4[C:14]3=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:28][OH:29]>C1(C)C=CC=CC=1.[O-2].[Cr+6].[O-2].[O-2]>[CH:24]1[C:25]2[C:12]3([C:13]4[CH:1]=[C:2]([CH:28]=[O:29])[CH:3]=[CH:4][C:5]=4[C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]=2[CH:21]=[CH:22][C:23]=1[CH:26]=[O:27]

Participants

4

Reactant 1

HCID 5249038HCID 5249038, compound

Product 1

HCID 11440186HCID 11440186, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 1140TolueneSolvent

Procedure

 A solution of 380 mg of 9,9′-spirobifluorene-2,2′-dimethanol in 15 ml of toluene was admixed with 5 g of chromium(VI) oxide on graphite (Seloxcette, Alpha Inorganics) and refluxed under nitrogen for 48 hours. The mixture was then filtered with suction on a glass suction filter and the filtrate was evaporated. Chromatography on silica gel using chloroform and crystallization from methylene chloride/ether gave 152 mg of 9,9′-spirobifluorene-2,2′-dicarbaldehyde (mp. >300° C.) and

Workup

  1. temperaturerefluxed under nitrogen for 48 hours
  2. filtrationThe mixture was then filtered with suction on a glass suction
  3. filtrationfilter
  4. customthe filtrate was evaporated
  5. customchloroform and crystallization from methylene chloride/ether

Sources & evidence

ORD record
ord-e8196f6ca8d84df4a9257e52767e0f05
Source dataset
uspto-grants-2004_11
Patent number
US06822094B2

Reaction notes

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