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

HRID 2426022

반응식

HRID 2426022 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, 1H), 6.81 (d, 1H), 5.11 (m, 1H), 3.86 (s, 6H), 2.30 (d, 1H), 1.48 (d, 3H).

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-7a1a98b2b4334265be402c99c68aeb87
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968538B2

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