Dimethyl Sulfate → 2-Methoxy-4-methylbenzonitrile

HRID 1157861

반응식

HRID 1157861 반응식
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].O.[OH-].[Li+].S(OC)(O[CH3:18])(=O)=O>C1COCC1.C(OCC)C>[CH3:18][O:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

참가 물질

6

반응물 3

HCID 6497Dimethyl SulfateHCID 168937Lithium hydroxide, monohydrateHCID 143886562-Hydroxy-4-methylbenzonitrile

생성물 1

HCID 124953732-Methoxy-4-methylbenzonitrile수율 90%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-Hydroxy-4-methylbenzonitrile (0.46 g, 3.46 mmol) in THF (17 mL) was added lithium hydroxide monohydrate (0.292 g, 6.95 mmol) followed by dimethyl sulfate (0.50 mL, 5.28 mmol). The resultant mixture was heated to reflux for 2 hours then cooled to room temperature. The mixture was diluted with diethyl ether (50 mL), washed with saturated aqueous NaHCO3 (3×15 mL), dried (MgSO4) and concentrated. Purification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc) provided 0.456 g (90%) of 2-methoxy-4-methylbenzonitrile as a white solid. 1H NMR (CDCl3) δ 2.41 (s, 3H), 3.91 (s, 3H), 6.77 (s, 1H), 6.81 (d, 1H, J=6 Hz), 7.43 (d, 1H, J=6 Hz). ES-MS m/z 148 (M+H).

후처리

  1. temperatureto reflux for 2 hours
  2. washwashed with saturated aqueous NaHCO3 (3×15 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc)

출처 및 근거

ORD 기록
ord-74005f83e0e34a329440f93292332fac
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807694B2

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