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

HRID 1427519노트

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HRID 1427519 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 (2.09 g, 12.7 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 h. The reaction was then quenched by addition of saturated aqueous ammonium chloride. This mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography gave methyl 4-(1-hydroxybutyl)benzoate (1.25 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 aqueous ammonium chloride
  2. extractionThis mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-d6bf17367afa4b738746b12d15245e71
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933104B2

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