Acetone → 4-Chloro-3,5-dimethylanisole

HRID 1070889

反応式

HRID 1070889 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 5984974-Chloro-3,5-dimethylanisole収率 77%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-4be58e7c21a04df98ea9e9504934580f
出典データセット
uspto-grants-2005_06
特許番号
US06903132B2

関連ノート

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