Dimethylformamide dimethyl acetal → Methyl 2-(cyanomethyl)benzoate

HRID 396214Notes

Reaction equation

HRID 396214 reaction equation
[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])#[N:2].[CH3:13]OC(OC)N(C)C>C(Cl)Cl>[CH3:13][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=1[CH2:3][C:1]#[N:2]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 811142-(Cyanomethyl)benzoic acid

Product 1

HCID 588805Methyl 2-(cyanomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

With gentle heating, 175 g (1.08 mol) of 2-cyanomethyl-benzoic acid (for preparation see: Org. Synthesis, Coll, Vol. 3,174) are dissolved in 1.7 liters of CH2Cl2; 242 ml (=90%, 1.6 mol) of dimethylformamide dimethylacetal are added dropwise at room temperature, and stirring is carried out for 38 hours to complete the reaction. The reaction mixture is washed with 2×1.2 liters of saturated NaHCO3 solution and brine. The aqueous phases are extracted using 2 portions of CH2Cl2, and the organic phases are dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; ethyl acetate/hexane 1:4, applied in ethyl acetate/hexane/CH2Cl2) yields the title compound: m.p. 49-50° C.; 1H NMR (DMSO-d6) 7.96 (d, 1H), 7.66 (t, 1H), 7.57 (d, 1H), 7.51 (t, 1H), 4.26 (s, 2H), 3.86 (s, 3H); Anal. calc. (C10H9NO2) C 68.56%, H 5.18%, N 8.00%; found C 68.5%, H 5.1%, N 7.9%.

Workup

  1. customthe reaction
  2. washThe reaction mixture is washed with 2×1.2 liters of saturated NaHCO3 solution and brine
  3. extractionThe aqueous phases are extracted
  4. dry with materialthe organic phases are dried (Na2SO4)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-bc4dc7d12901461e87d4019e43f4676b
Source dataset
uspto-grants-2003_08
Patent number
US06608071B2

Reaction notes

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