Water → Methyl (3-cyanophenyl)acetate

HRID 572928Notes

Reaction equation

HRID 572928 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].S(Cl)(Cl)=O.[CH3:17]N(C)C=O.O>CO>[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:17])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 15193972-(3-Cyanophenyl)acetic acid

Product 1

HCID 1514291Methyl (3-cyanophenyl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(3-cyanophenyl)acetic acid (1, 6.2 mmol) in methanol (20 ml) was added sulfurous dichloride (5 ml) and 0.1 ml N,N-dimethylformamide. Then the reaction mixture was heated to 80° C. for 2 h. When TLC indicated that the starting material was consumed, the mixture was concentrated to give the residue. The residue was poured into water (20 ml) and was extracted by ethyl acetate (50 m1*2). The organic layer was dried by anhydrous sodium sulfate, filtered, concentrated to give the desired product. LC-MS: m/z (M+H)=176.5

Workup

  1. customwas consumed
  2. concentrationthe mixture was concentrated
  3. customto give the residue
  4. extractionwas extracted by ethyl acetate (50 m1*2)
  5. dry with materialThe organic layer was dried by anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9e5ad3192a7f4da0baf665c5a14b78d3
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Reaction notes

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