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4-Hydroxybenzaldehyde → tert-Butyl 2-(4-formylphenoxy)-2-methylpropanoate

HRID 353166
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HRID 353166 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:17]([CH3:26])([CH3:25])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CN(C)C=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:17]([CH3:26])([CH3:25])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:3][CH:4]=1)=[O:7]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1264-HydroxybenzaldehydeHCID 10796Cesium carbonateHCID 90290tert-Butyl 2-bromo-2-methylpropionate

생성물 1

HCID 22708193tert-Butyl 2-(4-formylphenoxy)-2-methylpropanoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
90 °C

실험 절차

A solution of 24.4 g (200 mmol) of 4-hydroxybenzaldehyde in 100 ml of dimethylformamide is treated with 97.75 g (300 mmol) of caesium carbonate and stirred at 90° C. for 1 h. A solution of 66.93 g (300 mmol) of tert-butyl 2-bromisobutyrate in 100 ml of dimethylformamide is then added dropwise, and the mixture is stirred at 90° C. overnight. The dimethylformamide is distilled off under reduced pressure and the residue is then taken up in ethyl acetate, washed 2× with water, 2× with 1 N aqueous sodium hydroxide solution and 1× with sat. NaCl solution, dried over sodium sulphate and freed from the solvent under reduced pressure. This gives 16.6 g (31%) of tert-butyl 2-(4-formylphenoxy)-2-methylpropionate.

후처리

  1. stirringthe mixture is stirred at 90° C. overnight
  2. distillationThe dimethylformamide is distilled off under reduced pressure
  3. washwashed 2× with water, 2× with 1 N aqueous sodium hydroxide solution and 1× with sat. NaCl solution
  4. dry with materialdried over sodium sulphate

출처 및 근거

ORD 기록
ord-425ad289c5ba4e20b1b8ae6163dce817
출처 데이터셋
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06750236B2

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