Acetone → HCID 12892725, 화합물

HRID 1468216노트

반응식

HRID 1468216 반응식
C[C:2]1(C)[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH2:4][C:3]1=[O:10].Cl.[CH3:13]C(C)=O>[Cl-].[Na+].O>[CH3:9][C:6]1([CH:8]=[CH2:13])[CH2:7][CH2:2][C:3](=[O:10])[CH2:4][CH2:5]1

참가 물질

5

반응물 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 583881972,2,4,4-Tetramethylcyclohexan-1-one

생성물 1

HCID 12892725HCID 12892725, 화합물수율 94%

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

실험 절차

To a stirred solution of 2 (1.98 mmol, 360 mg) in acetone (7.76 mL) was added 10% aqueous hydrochloric acid solution (3.02 mL), and the resulting mixture was stirred at room temperature for 2.5 hours. The reaction mixture was then diluted with brine (40 mL) and extracted with methylene chloride/ethyl ether (1:2, 3×30 mL). The organic layers were combined and washed with saturated aqueous sodium bicarbonate solution (2×30 mL) and brine (1×30 mL), then dried over magnesium sulfate, filtered, and concentrated in vacuo to give 19 (251.6 mg, 1.92 mmol, 94%) as a yellow oil that was used in the next reaction without further purification: 1H NMR (CDCl3) δ 5.89 (1H, dd, J=0.5, 17.3 Hz), 5.15 (1H, dd, J=1, 3.5 Hz), 5.12 (1H, dd, J=0.5, 10 Hz), 2.42-2.28 (4H, m), 1.97-1.91 (2H, m), 1.74-1.68 (2H, m), 1.12 (3H, s); 13C NMR (CDCl3) δ 212.4, 145.5, 112.9, 38.2, 37.1, 27.4; MS (EI) m/z 138.1 [M+], 123.1, 110.1, 105.1, 97.1, 86.0 (100%), 68.1, 63.0, 54.9; HRMS (EI) calcd for C9H14O 138.1045 found 138.1048.

후처리

  1. extractionextracted with methylene chloride/ethyl ether (1:2, 3×30 mL)
  2. washwashed with saturated aqueous sodium bicarbonate solution (2×30 mL) and brine (1×30 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-26430c305a444f9e821d0fa7ff3ed3ba
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000188B2

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