Methanol → 2-(Methyloxy)-4-(2-oxoethyl)benzonitrile

HRID 1465782Notes

Reaction equation

HRID 1465782 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH2:11][CH:12]=C)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].CSC.C[OH:18]>>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH2:11][CH:12]=[O:18])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 666438682-(Methyloxy)-4-prop-2-en-1-ylbenzonitrile

Product 1

HCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrile

Procedure

To a 25 mL flask containing a stir bar was added compound 2-(methyloxy)-4-prop-2-en-1-ylbenzonitrile (0.15 g, 0.87 mmol) and MeOH (8 mL). The flask was placed in a cold bath of −78° C. Ozone was bubbled through the flask for about 10 min. followed by addition of dimethyl sulfide (1.5 mL, 24 mmol). The flask was taken out of the cold bath and stirred at room temperature for 1 h; LC indicated completion of the reaction. The reaction mixture was concentrated to dryness to give 2-(methyloxy)-4-(2-oxoethyl)benzonitrile. LC-MS (IE, m/z): 176 [M+1]+.

Workup

  1. additionTo a 25 mL flask containing a stir bar
  2. customThe flask was placed in a cold bath of −78° C
  3. customOzone was bubbled through the flask for about 10 min.
  4. customcompletion of the reaction
  5. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-d762e888fc9247a58be9702fee0d6094
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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