Acetone → 2,4-Pentanedione, 1-phenyl-

HRID 42482

반응식

HRID 42482 반응식
[C:1]1([CH2:7][C:8]([O:10]CC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][C:14]([CH3:16])=[O:15].Cl>CCOCC>[C:1]1([CH2:7][C:8](=[O:10])[CH2:13][C:14](=[O:15])[CH3:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 7590Ethyl phenylacetate

생성물 1

HCID 187232,4-Pentanedione, 1-phenyl-수율 69.3%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of NaNH2 (19.02 g, 480 mmol) in anhydrous ether (400 mL) under N2 at −5° C. was added dropwise ethyl phenylacetate (19.2 g, 150 mmol) and then acetone (21.23 g, 370 mmol) with vigorous stirring. After addition, the reaction mixture was stirred at room temperature overnight. The mixture was then acidified to pH 4.0-5.0 with 1N HCl. The organic layer was separated and concentrated in vacuo. The crude product was purified by silica gel chromatography to give 1-phenyl-2,4-pentanedione (18.32 g, 44%). 1H NMR (400 MHz, CDCl3-d3) δ 15.49 (br s, 1H), 7.33-7.45 (m, 5H), 5.53 (s, 1H), 3.66 (s, 2H), 2.10 (s, 3H).

후처리

  1. additionAfter addition
  2. customThe organic layer was separated
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-0ec4b86d59ec4f84873870f94c1bb870
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536179B2

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