Mesitylene → Benzenemethanol, 3,5-dimethyl-, 1-acetate

HRID 1885070Notes

Reaction equation

HRID 1885070 reaction equation
C1(C)C=C(C)C=C(C)C=1.N([O:12][C:13](C)(C)[CH3:14])=O.ON1C(=O)C2=CC=CC=C2C1=O.CC1C=C(C=C(C)C=1)C=NO.[CH3:40][C:41]1[CH:42]=[C:43]([CH:46]=[C:47]([CH3:49])[CH:48]=1)[CH:44]=[O:45].CC1C=C(C=C(C)C=1)C#N>C(O)(=O)C>[C:13]([O:45][CH2:44][C:43]1[CH:46]=[C:47]([CH3:49])[CH:48]=[C:41]([CH3:40])[CH:42]=1)(=[O:12])[CH3:14]

Participants

8

Reactant 6

HCID 7947MesityleneHCID 10665N-HydroxyphthalimideHCID 10906Tert-Butyl nitriteHCID 34225Benzaldehyde, 3,5-dimethyl-HCID 897183,5-DimethylbenzonitrileHCID 71401900N-[(3,5-Dimethylphenyl)methylidene]hydroxylamine

Product 1

HCID 12229212Benzenemethanol, 3,5-dimethyl-, 1-acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Mesitylene (1 ml), t-butyl nitrite (1 mmol), N-hydroxyphthalimide (0.2 mmol), and acetic acid (1 ml) were placed in a flask and were stirred at 60° C. in an atmosphere of argon gas (1 atm=0.101 MPa) for 20 hours. The resulting reaction mixture was analyzed to find that 3,5-dimethylbenzaldehyde oxime, 3,5-dimethylbenzaldehyde, 3,5-dimethylbenzonitrile, and 3,5-dimethylphenylmethyl acetate were formed in yields of 61%, 3%, 4%, and less than 1%, respectively.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-6dbe78615a4b4b198597b09087a4073c
Source dataset
uspto-grants-2004_07
Patent number
US06768023B2

Reaction notes

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