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

HRID 1910647노트

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HRID 1910647 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.CCOCC.[Cl-].[NH4+]>CC(OC)(C)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

6

반응물 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 41722755-Chloro-2,3-dimethoxybenzaldehydeHCID 178418573HCID 178418573, 화합물2회

생성물 1

HCID 140929151-(5-Chloro-2,3-dimethoxyphenyl)ethanol수율 96%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

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온도
33 °C

실험 절차

To a mixture of 5-chloro-2,3-dimethoxybenzaldehyde (339, 1.69 mol) in TBME (5.6 L) was added 3M methylmagnesium bromide in ether (660 mL, 1.98 mol) over 1 hour at 9 to 12° C. The mixture was warmed at 33° C. for 1 hour 20 minutes. There was significant starting material present so more methylmagnesium bromide was added (590 mL, 1.77 mol) over 1 hour 20 minutes with the reaction temperature at 33° C. The reaction was cooled to room temperature overnight and poured into ammonium chloride (20 wt %, 3 kg) over 5 minutes. The temperature rose from 11 to 28° C. The reaction flask was rinsed with ammonium chloride solution (500 mL) and TBME (250 mL). The layers were separated and the organic layer was concentrated to an orange yellow thick oil. Yield: 348 g (96% yield, 94% purity).

후처리

  1. additionwas added (590 mL, 1.77 mol) over 1 hour 20 minutes with the reaction temperature at 33° C
  2. temperatureThe reaction was cooled to room temperature overnight
  3. customrose from 11 to 28° C
  4. washThe reaction flask was rinsed with ammonium chloride solution (500 mL) and TBME (250 mL)
  5. customThe layers were separated
  6. concentrationthe organic layer was concentrated to an orange yellow thick oil

출처 및 근거

ORD 기록
ord-f6e6fe890c894580bd2710ff3326b314
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604021B2

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