Hydrochloric Acid → 2-(4-Methoxyphenyl)cyclohexanone

HRID 418913

반응식

HRID 418913 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10]1(=[O:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.CC(C)([O-])C.[Na+].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C:10]2=[O:16])=[CH:3][CH:4]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 77304-BromoanisoleHCID 7967CyclohexanoneHCID 23676156Sodium t-butoxide

생성물 1

HCID 2542922-(4-Methoxyphenyl)cyclohexanone수율 38.4%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

Combine 4-bromoanisole (19.6 g, 104 mmol), cyclohexanone (13.2 g, 136 mmol), sodium tert-butoxide (11.8 g, 120 mmol), palladium acetate (0.47 g, 2.1 mmol), (oxy-di-2,1-phenylene)bis-diphenylphosphine (2.28 g, 4.1 mmol) and toluene (240 mL) and heated at 90° C. under nitrogen. After 18 hours, cool to room temperature and add 1N HCl (120 mL). Extract with methylene chloride and wash the combined extracts with brine. Dry the organic layer over sodium sulfate and concentrate in vacuo. Purify by flash chromatography using silica gel and 10% ethyl acetate-hexanes to yield the titled compound (8.15 g, 38%) as a white solid. 1H NMR (CDCl3) δ 7.12 (d, 2H, J=7.5 Hz), 6.92 (d, 2H, J=7.5 Hz), 3.84 (s, 3 H), 3.59 (dd, 1H, J=8.0 and 3.5 Hz), 2.60-2.45 (m, 2H), 2.29 (m, 1H), 2.18 (m, 1H), 2.04 (m, 2H), 1.85 (m, 2H). MS m/z 205 (M+1).

후처리

  1. extractionExtract with methylene chloride
  2. washwash the combined extracts with brine
  3. dry with materialDry the organic layer over sodium sulfate
  4. concentrationconcentrate in vacuo
  5. customPurify by flash chromatography

출처 및 근거

ORD 기록
ord-3913baa3e50e4a58b0542ab5d19ebd54
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093302B2

연결된 노트

불러오는 중…