AE-646/11813021 → carboxycubane

HRID 2209408Notes

Reaction equation

HRID 2209408 reaction equation
C1[O:5][C:4]2([C:9]3(Br)[CH:10]4[CH:13]5[CH:6]2[CH:7]2C(=O)[C:12]5(Br)[CH:11]4[CH:8]23)[O:3]C1>[OH-].[K+]>[C:9]12([C:4]([OH:3])=[O:5])[CH:8]3[CH:7]4[CH:12]5[CH:11]3[CH:10]1[CH:13]5[CH:6]24

Participants

3

Reactant 1

HCID 429365AE-646/11813021

Product 1

HCID 10997192carboxycubane

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Cubanecarboxylic acid (53578-15-7) (33) is obtained from (32) by the method of Eaton and Cole, by refluxing the ketal in 25% aqueous KOH overnight. Extraction with methylene chloride, drying over magnesium sulfate, stripping the solvent, and recrystallization from pentane yields (33), mp 154°-155° C.; λmax (CCl4) 5.91μ; proton NMR (CCl4, ppm τ): -2.2(1H, s) , and 5.6-6.2(7H, m).

Workup

  1. extractionExtraction with methylene chloride
  2. dry with materialdrying over magnesium sulfate
  3. customthe solvent, and recrystallization from pentane

Sources & evidence

ORD record
ord-c34a073fbaf949b88af1c3323fe69644
Source dataset
uspto-grants-1995_10
Patent number
US05455072

Reaction notes

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