Water → Methyl 2,5-dimethylbenzoate

HRID 1972131

反応式

HRID 1972131 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[CH3:12][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=1[CH3:1]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 118922,5-Dimethylbenzoic acid

生成物 1

HCID 273300Methyl 2,5-dimethylbenzoate収率 97.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Into a suspension of 75 g (499 mmol) 2,5-dimethylbenzoic acid, 103 g (748 mmol) potassium carbonate in 500 mL of DMF was added dropwise 77.9 g (549 mmol) of iodomethane with stirring at ambient temperature. After addition, the suspension was stirred for additional 5 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate. All solids were removed by filtration and the filtrate was concentrated to 80 g of colorless oil as product in 97.6% yield. 1H NMR (CDCl3) (300 MHz) δ 2.7 (s, 3H), 2.8 (s, 3H), 3.95 (s, 3H), 7.45 (s 1H), 7.51 (d, 3JHCCH=7.9 Hz, 1H), 7.42 (d, 3JHCCH=7.9 Hz, 1H)

後処理

  1. additionAfter addition
  2. stirringthe suspension was stirred for additional 5 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAll solids were removed by filtration
  7. concentrationthe filtrate was concentrated to 80 g of colorless oil as product in 97.6% yield

出典と根拠

ORDレコード
ord-1a83d3cd0f154b67ba4fb0c6403b162e
出典データセット
uspto-grants-2013_04
特許番号
US08431721B2

関連ノート

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