Dichloromethane → Methyl 4-cyano-3-methylbenzoate

HRID 220766Notes

Reaction equation

HRID 220766 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[CH3:12])#[N:2].S(Cl)(Cl)=O.Cl[CH2:18]Cl>>[CH3:18][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[C:4]([CH3:12])[CH:5]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 102410994-Cyano-3-methylbenzoic acid

Product 1

HCID 19969932Methyl 4-cyano-3-methylbenzoateYield 100%

Procedure

A mixture of 4-cyano-3-methyl-benzoic acid from Example E2d (1.5 g, 9.3 mmol) and thionyl chloride (5 ml, 68.5 mmol) in dichloromethane (20 ml) was heated at re-flux for 2 h then solvents were removed in vacuo and azeotroped with toluene. The residue was redissolved in dichloromethane (25 ml). Methanol (10 ml) was added and the solution was stirred at room temperature for 2 h then concentrated in vacuo. The residue was redissolved in EtOAc, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo to yield the title compound (1.6 g, 100%).

Workup

  1. temperaturewas heated at re-flux for 2 h
  2. customsolvents were removed in vacuo
  3. customazeotroped with toluene
  4. dissolutionThe residue was redissolved in dichloromethane (25 ml)
  5. additionMethanol (10 ml) was added
  6. concentrationthen concentrated in vacuo
  7. dissolutionThe residue was redissolved in EtOAc
  8. washwashed with saturated NaHCO3
  9. dry with materialbrine, dried
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f75b35647a4480cb5c99bc29b1550ee
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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