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

HRID 546100ノート

反応式

HRID 546100 の反応式
[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

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 243003Methyl 2-formylbenzoateHCID 178455855HCID 178455855、化合物

生成物 1

HCID 10443031Methyl 4-(1-hydroxybutyl)benzoate収率 48%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-60d78cb277564d268d4b2a674ca05971
出典データセット
uspto-grants-2011_05
特許番号
US07935699B2

反応ノート

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