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

HRID 1910580

반응식

HRID 1910580 반응식
[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

참가 물질

4

반응물 2

HCID 41722755-Chloro-2,3-dimethoxybenzaldehydeHCID 178418573HCID 178418573, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ecdf62a3bd264499b0564affada312f0
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604021B2

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