Iodine → 2-(2-Ethylphenyl)ethanol

HRID 870464

반응식

HRID 870464 반응식
N#N.II.Br[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH3:13].[O:14]1[CH2:16][CH2:15]1>C1COCC1>[CH2:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:16][CH2:15][OH:14])[CH3:13]

참가 물질

6

반응물 4

HCID 807IodineHCID 947NitrogenHCID 6354Ethylene OxideHCID 160891-Bromo-2-ethylbenzene

생성물 1

HCID 149074472-(2-Ethylphenyl)ethanol수율 63%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

Into a 250-mL round-bottom flask protected by N2 was placed tetrahydrofuran (100 mL), Mg (1.0 g, 41.67 mmol, 2.14 equiv) and I2 (0.010 g). Then a solution of 1-bromo-2-ethylbenzene (3.6 g, 19.45 mmol, 1.00 equiv) in THF (15 mL) was added dropwise. The resulting mixture was heated to reflux for 1 h. Then it was cooled to 0° C. and oxirane (50 mL) was added. The resulting solution was stirred at room temperature overnight. The reaction was then quenched by the addition of 20 mL of NH4Cl (aq.). The resulting solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). Purification afforded 1.83 g (63%) of 2-(2-ethylphenyl)ethan-1-ol as a colorless oil.

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 1 h
  3. customThe reaction was then quenched by the addition of 20 mL of NH4Cl (aq.)
  4. extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
  5. concentrationconcentrated under vacuum
  6. customPurification

출처 및 근거

ORD 기록
ord-48ced848e0db4e16a070e5e6ea63278d
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969557B2

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