Dichloromethane → Methyl 4-cyano-3-methylbenzoate

HRID 220766노트

반응식

HRID 220766 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6f75b35647a4480cb5c99bc29b1550ee
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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