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

HRID 1910647ノート

反応式

HRID 1910647 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.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

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 41722755-Chloro-2,3-dimethoxybenzaldehydeHCID 178418573HCID 178418573、化合物2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
33 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f6e6fe890c894580bd2710ff3326b314
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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