Methyl 4-(1-hydroxybutyl)-3-methylbenzoate → Methyl 4-butyryl-3-methylbenzoate

HRID 537457

反応式

HRID 537457 の反応式
[OH:1][CH:2]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[CH3:16])[CH2:3][CH2:4][CH3:5]>ClCCl.[O-2].[O-2].[Mn+4]>[C:2]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[CH3:16])(=[O:1])[CH2:3][CH2:4][CH3:5]

参加物

4

反応物 1

HCID 68178586Methyl 4-(1-hydroxybutyl)-3-methylbenzoate

生成物 1

HCID 68157866Methyl 4-butyryl-3-methylbenzoate収率 32.9%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 6344Dichloromethane溶媒

反応条件

温度
30 °C

実験手順

To a solution of (+/−)-methyl 4-(1-hydroxybutyl)-3-methylbenzoate (0.8 g, 4 mmol) in dichloromethane (15 mL) was added manganese dioxide (3.13 g, 36.0 mmol). The reaction was stirred at 30° C. overnight. TLC showed starting material remained and the reaction was heated to reflux for 5 hours. The reaction was cooled to room temperature and filtered through Celite. The filtrate was concentrated and purified by flash column chromatography to give methyl 4-butyryl-3-methylbenzoate (290 mg) as an oil. 1H NMR (400 MHz, CDCl3, δ): 7.90 (d, J=7.6 Hz, 2H), 7.59 (d, J=7.6 Hz, 1H), 3.93 (s, 3H), 2.86 (t, J=7.6 Hz, 2H), 2.49 (s, 3H), 1.69-1.78 (m, 2H), 0.99 (t, J=7.6 Hz, 3H).

後処理

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 5 hours
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationfiltered through Celite
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash column chromatography

出典と根拠

ORDレコード
ord-e9bac1529aae471cab60aa395555b6d3
出典データセット
uspto-grants-2014_10
特許番号
US08859591B2

関連ノート

読み込み中…