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Water → Ethyl 2-(3-formylphenoxy)acetate

HRID 592073
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HRID 592073 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:6]
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참가 물질

5

반응물 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 1317345403-Hydroxy benzaldehyde ethyl 2-bromoacetate

생성물 1

HCID 1494377Ethyl 2-(3-formylphenoxy)acetate수율 23%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

3-hydroxy benzaldehyde/ethyl 2-bromoacetate (1.1 eq) and K2CO3 (2 eq) were taken in DMF and heated at 80° C. for 16 h when TLC indicated completion of reaction. The reaction mixture was cooled to rt and poured into water. Extraction was done with DCM. The combined organic extracts was dried, concentrated and purified by column chromatography using silica gel (100-200 mesh) to afford the pure product (23%) as a colorless oil. NMR: δ 1.298 (t, J=7.2 Hz, 3H), 4.27 (q, J=7.2 Hz, 2H), 4.683 (s, 1H), 7.20-7.27 (m, 1H), 7.361 (s, 1H), 7.42-7.52 (m, 2H), 9.96 (s, 1H).

후처리

  1. customcompletion of reaction
  2. temperatureThe reaction mixture was cooled to rt
  3. extractionExtraction
  4. customThe combined organic extracts was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-c91c6ea9d1bf47858af8a512b83cc93f
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238656B2

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