5-Chloro-2,3-dimethoxybenzaldehyde → 1-(5-Chloro-2,3-dimethoxyphenyl)ethanol

HRID 1910580ノート

反応式

HRID 1910580 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:14][Mg]Br>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:7]([OH:8])[CH3:14])[CH:9]=1

参加物

4

反応物 2

HCID 41722755-Chloro-2,3-dimethoxybenzaldehydeHCID 178418573HCID 178418573、化合物

生成物 1

HCID 140929151-(5-Chloro-2,3-dimethoxyphenyl)ethanol収率 75%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

To a stirred solution of 5-chloro-2,3-dimethoxy-benzaldehyde (7.0 g, 34.90 mmol) in dry diethyl ether (500 mL) at 0° C. was added methylmagnesium bromide of 3.0 M in diethyl ether (29 mL, 87.22 mmol). The reaction mixture was brought to room temperature and stirred for 30 min; refluxed for 3 h; then cooled to 0° C. and quenched by adding saturated aqueous NH4Cl. The two liquid layers were separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water, dried, and concentrated to the crude compound which was purified by silica gel column (10-25% ethyl acetate in hexanes) to afford 1-(5-chloro-2,3-dimethoxy-phenyl)-ethanol (5.67 g, 75%): 1H NMR (400 MHz, CDCl3): δ 7.00 (d, 1 H), 6.81 (d, 1 H), 5.11 (m, 1 H), 3.86 (s, 6 H), 2.30 (d, 1 H), 1.48 (d, 3 H).

後処理

  1. customwas brought to room temperature
  2. temperaturerefluxed for 3 h
  3. customquenched
  4. additionby adding saturated aqueous NH4Cl
  5. customThe two liquid layers were separated
  6. extractionThe aqueous layer was extracted with diethyl ether
  7. washThe combined organic layers were washed with water
  8. customdried
  9. concentrationconcentrated to the crude compound which
  10. customwas purified by silica gel column (10-25% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-ecdf62a3bd264499b0564affada312f0
出典データセット
uspto-grants-2013_12
特許番号
US08604021B2

反応ノート

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