Methyl 4-Formylbenzoate → Methyl 4-(1-hydroxybutyl)benzoate

HRID 537434노트

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HRID 537434 반응식
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=[O:2].[CH2:13]([Mg]Br)[CH2:14][CH3:15]>O1CCCC1>[OH:2][CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[CH2:13][CH2:14][CH3:15]

참가 물질

4

반응물 2

HCID 15294Methyl 4-FormylbenzoateHCID 178455851HCID 178455851, 화합물

생성물 1

HCID 10443031Methyl 4-(1-hydroxybutyl)benzoate수율 47%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of methyl 4-formylbenzoate (2.092 g, 12.74 mmol) in tetrahydrofuran (50 mL) was cooled to 0° C. To this solution was added n-propylmagnesium bromide (6.4 mL, 2.0M in THF) dropwise over 20 minutes. The reaction was stirred at 0° C. for 2 hours. The reaction was then quenched by addition of saturated ammonium chloride. This mixture was extracted with ethyl acetate twice. The organics were dried over magnesium sulfate, filtered and concentrated. Purification by column chromatography (0-40% ethyl acetate in heptanes) gave (+/−)-methyl 4-(1-hydroxybutyl)benzoate (1.252 g, 47%) as a colorless oil. 1H NMR (400 MHz, CDCl3, δ): 7.97-8.02 (m, 2H), 7.40 (d, J=8.4 Hz, 2H), 4.74 (dd, J=7.8, 5.7 Hz, 1H), 3.90 (s, 3H), 1.61-1.82 (m, 2H), 1.23-1.49 (m, 2H), 0.92 (t, J=7.32 Hz, 3H).

후처리

  1. customThe reaction was then quenched by addition of saturated ammonium chloride
  2. extractionThis mixture was extracted with ethyl acetate twice
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (0-40% ethyl acetate in heptanes)

출처 및 근거

ORD 기록
ord-b7ac043a425c4ebda596b7b4af2d979c
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859591B2

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