Dimethyl Sulfate → 1-Chloro-2-methoxy-4-methylbenzene

HRID 83855

반응식

HRID 83855 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[CH3:10]OS(OC)(=O)=O.C([O-])([O-])=O.[K+].[K+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10]

참가 물질

4

반응물 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 120082-Chloro-5-methylphenol

생성물 1

HCID 993521-Chloro-2-methoxy-4-methylbenzene

실험 절차

To a solution of 2-chloro-5-methylphenol (10) (250 g, 1.75 mol) in CH3N (2.5 L) was added Me2SO4 (184 mL, 1.93 mol) and K2CO3 (314 g, 2.28 mol). The reaction mixture was heated to reflux for 6 h with mechanical stirring. The reaction mixture was cooled to ambient temperature and filtered through Celite. The filtrate was evaporated. The residue was diluted with EtOAc (1.5 L), washed with water (1.5 L*2) and brine (1.5 L) successively, dried over MgSO4, filtered and concentrated under reduced pressure to give 2-chloro-5-methylanisole (11) as a light yellow oil (274 g, quantitative). 1H NMR (400 MHz, CDCl3): δ 7.20-7.25 (d, 1H), 6.73 (s, 1H), 6.68-6.71 (d, 1H), 3.86 (s, 3H), 2.31 (s, 3H).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 h with mechanical stirring
  3. filtrationfiltered through Celite
  4. customThe filtrate was evaporated
  5. additionThe residue was diluted with EtOAc (1.5 L)
  6. washwashed with water (1.5 L*2) and brine (1.5 L) successively
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a59ceee5f8e649f4b3c80dedded1d8c3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846739B2

연결된 노트

불러오는 중…