Oxygen → 4-tert-Butylbenzaldehyde

HRID 1960157Notes

Reaction equation

HRID 1960157 reaction equation
C(C1C=CC(C)=CC=1)(C)(C)C.ON1C(=O)C2=CC=CC=C2C1=O.O=O.[C:26]([C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1)([CH3:29])([CH3:28])[CH3:27]>C(O)(=O)C>[C:26]([C:30]1[CH:31]=[CH:32][C:33]([CH:34]=[O:35])=[CH:37][CH:38]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 977OxygenHCID 73904-tert-ButyltolueneHCID 74034-tert-Butylbenzoic acidHCID 10665N-Hydroxyphthalimide

Product 1

HCID 703244-tert-Butylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 3 mL of acetic acid was dissolved 300 mg of p-t-butyltoluene to give a solution, and the solution was further combined with 150 mg of the catalyst A and 33 mg of N-hydroxyphthalimide, followed by stirring at 100° C. in an oxygen atmosphere for 6 hours. The reaction mixture was analyzed through gas chromatography to find that p-t-butylbenzoic acid and p-t-butylbenzaldehyde were obtained in yields of 66.5% and 3.8%, respectively, with a conversion from p-t-butyltoluene of 82.2%. The catalyst A was separated from the reaction mixture through filtration, washed with ethyl acetate two times, dried at room temperature (25° C.) under reduced pressure, and recovered as a catalyst A1. The cobalt ion concentration in the reaction mixture, from which the catalyst A1 had been separated through filtration, was measured through atomic absorption spectrometry and was found to be 24 ppm.

Workup

  1. customto give a solution

Sources & evidence

ORD record
ord-372e9163a0b944958962306d959ca0a2
Source dataset
uspto-grants-2013_04
Patent number
US08410308B2

Reaction notes

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