HCID 5249038, compound → HCID 11440186, compound

HRID 635124Notes

Reaction equation

HRID 635124 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].[OH:29][CH2:28][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([C:12]4([C:25]5[CH:24]=[C:23]([CH:26]=[O:27])[CH:22]=[CH:21][C:20]=5[C:19]5[C:14]4=[CH:15][CH:16]=[CH:17][CH:18]=5)[C:13]=2[CH:1]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

5

Reactant 1

HCID 5249038HCID 5249038, compound

Product 2

HCID 11440186HCID 11440186, compoundHCID 22016048HCID 22016048, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 1140TolueneSolvent

Procedure

5 g of chromium(VI) oxide on graphite (Seloxcette, Alpha Inorganics) were added to a solution of 380 mg of 9,9′-spirobifluorene-2,2′-dimethanol in 15 ml of toluene, and the mixture was refluxed under nitrogen for 48 h. The mixture was then filtered with suction using a glass suction filter, and the filtrate was evaporated. Chromatography on silica gel using chloroform and crystallization from methylene chloride/ether produced 152 mg of 9,9′-spirobifluorene-2,2′-dicarbaldehyde (m.p. >300° C.) and 204 mg of 2′-hydroxymethyl-9,9′-spirobifluorene-2-carbaldehyde (m.p. 262 to 263° C.).

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 48 h
  2. filtrationThe mixture was then filtered with suction
  3. filtrationfilter
  4. customthe filtrate was evaporated
  5. customchloroform and crystallization from methylene chloride/ether

Sources & evidence

ORD record
ord-fab3f3a39c5f4c6c9c3072646b4ad7ce
Source dataset
uspto-grants-2001_02
Patent number
US06187224B1

Reaction notes

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