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

HRID 1520831

반응식

HRID 1520831 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

HCID 68157866Methyl 4-butyryl-3-methylbenzoate수율 32.9%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6344Dichloromethane용매

반응 조건

온도
30 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4ccd4c87fa48499f8d54c16602468f8f
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073871B2

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