Hydrochloric Acid → Methyl 4-(1-hydroxybutyl)benzoate

HRID 546100노트

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HRID 546100 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1C=O.[CH2:13]([Mg]Cl)[CH2:14]C.C([O:20][CH2:21][CH3:22])C.Cl>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[CH:6][C:7]([CH:21]([OH:20])[CH2:22][CH2:13][CH3:14])=[CH:8][CH:9]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 243003Methyl 2-formylbenzoateHCID 178455855HCID 178455855, 화합물

생성물 1

HCID 10443031Methyl 4-(1-hydroxybutyl)benzoate수율 48%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

Formyl-benzoic acid methyl ester (1.00 g, 6.10 mmol) was dissolved in tetrahydrofuran (15 mL), under argon, and chilled to 0° C. A 2.0 M solution of propyl magnesium chloride in diethyl ether (3.05 mL, 6.1 mmol) was added dropwise and the reaction continued to stir at 0° C. for 45 min. 1.0 M aqueous hydrochloric acid solution (10 mL) was added to the reaction and the solution stirred vigorously for 10 min. The solution was diluted with ethyl acetate (100 mL), washed with 1.0 M aqueous hydrochloric acid solution (20 mL), saturated aqueous brine solution (10 mL), dried over magnesium sulfate and concentrated in vacuo to a clear oil. Purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 25% ethyl acetate/hexanes) afforded 4-(1-hydroxy-butyl)-benzoic acid methyl ester (610 mg, 48%) as a clear oil: H1-NMR (400 MHz, CDCl3) δ 0.94 (3H, t, J=7.2 Hz), 1.22-1.52 (2H, m), 1.62-1.84 (2H, m), 2.00 (1H, s), 3.91 (3H, s), 4.74 (1H, t, J=6.8 Hz), 7.40 (2H, d, J=8.4 Hz), 7.99 (2H, d, J=8.0 Hz).

후처리

  1. stirringthe solution stirred vigorously for 10 min
  2. washwashed with 1.0 M aqueous hydrochloric acid solution (20 mL), saturated aqueous brine solution (10 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo to a clear oil
  5. customPurification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 25% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-60d78cb277564d268d4b2a674ca05971
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935699B2

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