tert-Butyl hydroperoxide → Benzoic Acid

HRID 654004Notes

Reaction equation

HRID 654004 reaction equation
C(=C1C=CC(C([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)=O)=CC1)C1C=CC=CC=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(OO)(C)(C)C>C1COCC1>[C:18]([OH:20])(=[O:19])[C:17]1[CH:21]=[CH:22][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 682631,1'-CarbonyldiimidazoleHCID 57040935HCID 57040935, compound

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To an ice cooled solution of 4-(4'-benzylidene benzoyl)-benzoic acid (1.40g) in THF was added a solution of 1,1'-carbonyldiimidazole (0.7g) in THF (10ml), with stirring. After 2 hours, a solution of t-butylhydroperoxide (0.5g of 80%) in THF (10ml) was added slowly. Stirring was continued for a further hour at 0° C. after which the solution was filtered and the solvent removed. The resulting oil was purified by column chromatography (silica) using dichloromethane as eluant. The resultant colourless oil solidified on overnight refrigeration to give a product having a melting point of 72°-76° C.

Workup

  1. stirringStirring
  2. waitwas continued for a further hour at 0° C.
  3. filtrationafter which the solution was filtered
  4. customthe solvent removed
  5. customThe resulting oil was purified by column chromatography (silica)
  6. waitThe resultant colourless oil solidified on overnight
  7. customrefrigeration to give a product

Sources & evidence

ORD record
ord-0829a81649434dcc964cb12abf35b089
Source dataset
uspto-grants-1992_07
Patent number
US05130227

Reaction notes

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