Acetone → 4-Chloro-3,5-dimethylanisole

HRID 1070889노트

반응식

HRID 1070889 반응식
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[CH3:11]C(C)=O.C(=O)([O-])[O-].[K+].[K+].IC>O>[CH3:11][O:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Cl:1])=[C:3]([CH3:10])[CH:4]=1

참가 물질

6

반응물 4

HCID 180AcetoneHCID 27234-Chloro-3,5-dimethylphenolHCID 6328Methyl iodideHCID 11430Potassium Carbonate

생성물 1

HCID 5984974-Chloro-3,5-dimethylanisole수율 77%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a 1 L round-bottom flask 4-chloro-3,5-dimethylphenol 63 (20 g, 127.7 mmol) and acetone (500 mL, 0.2 M) was placed. To this solution were added potassium carbonate (35.3 g, 255.4 mmol) and iodomethane (63.44 g, 447 mmol). The reaction was stirred and heated to reflux for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate and concentrated. The crude product was purified by silica gel chromatography eluted with hexane to yield 4-chloro-3,5-dimethylphenyl methyl ether 64 (16.88 g, 77%). 1HNMR (300 MHz, CDCl3): δ 2.41 (s, 3H), 2.59 (s, 3H), 2.62 (s, 3H), 2.68 (s, 3H), 3.82 (s, 3H), 4.06 (s, 3H), 4.11 (s, 2H), 5.97 (d, 1H), 6.44 (s, 1H), 6.70 (s, 1H), 7.15 (d, 1H), 8.41 (brd, 1H), 10.31 (brd, 1H), APCI-MS m/z 468.2 (M+H)+.

후처리

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography
  8. washeluted with hexane

출처 및 근거

ORD 기록
ord-4be58e7c21a04df98ea9e9504934580f
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903132B2

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