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

HRID 83855

反応式

HRID 83855 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a59ceee5f8e649f4b3c80dedded1d8c3
出典データセット
uspto-grants-2014_09
特許番号
US08846739B2

関連ノート

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