Methyl Acrylate → Benzeneacetonitrile, 3-(methylthio)-

HRID 657505Notes

Reaction equation

HRID 657505 reaction equation
CS[C:3]1[CH:4]=[C:5]([CH2:9]O)C=C[CH:8]=1.[CH3:11][S:12][C:13]1[CH:14]=[C:15]([CH2:19][C:20]#[N:21])[CH:16]=[CH:17][CH:18]=1.C(OC)(=[O:25])C=C>>[CH3:11][S:12][C:13]1[CH:14]=[C:15]([CH2:19][C:20]#[N:21])[CH:16]=[CH:17][CH:18]=1.[CH3:11][S:12][C:13]1[CH:14]=[C:15]([C:19]2([C:20]#[N:21])[CH2:9][CH2:5][C:4](=[O:25])[CH2:3][CH2:8]2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 11094968Benzeneacetonitrile, 3-(methylthio)-HCID 122557423-(Methylthio)benzyl alcohol

Product 2

HCID 11094968Benzeneacetonitrile, 3-(methylthio)-HCID 594425831-(3-Methylsulfanylphenyl)-4-oxocyclohexanecarbonitrile

Procedure

The title compound was prepared according to the process described in Example 183 via the intermediates (3-methylsulfanylphenyl)methanol (MS (ESI+): 155) and (3-methylsulfanylphenyl)acetonitrile (MS (ESI+): 164). In step c), the reaction mixture was not heated under reflux after the addition of the methyl acrylate, but stirred for 16 h at room temperature. From 2.9 g of (3-methylsulfanylphenyl)acetonitrile, 0.85 g of the title compound was obtained.

Workup

  1. customThe title compound was prepared
  2. temperatureIn step c), the reaction mixture was not heated
  3. temperatureunder reflux

Sources & evidence

ORD record
ord-735915b8a367466aa027bfc4dac26fed
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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