Hydrochloric Acid → 2-(4-Methoxyphenyl)cyclohexanone

HRID 418913

反応式

HRID 418913 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 2542922-(4-Methoxyphenyl)cyclohexanone収率 38.4%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3913baa3e50e4a58b0542ab5d19ebd54
出典データセット
uspto-grants-2012_01
特許番号
US08093302B2

関連ノート

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