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

HRID 2173212Notes

Reaction equation

HRID 2173212 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 (0.150 g, 0.866 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, 0.024 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-5d2709dcd73d4967a04ea12831c9aaf0
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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