Isopropanol → 4,4,6-Trimethyl-1,2,3,4-tetrahydronaphthalen-1-one

HRID 915177

反応式

HRID 915177 の反応式
[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[CH2:5][CH2:4][CH2:3]1.C([OH:17])(C)C>C(O)(=O)C.O.[O-2].[Cr+6].[O-2].[O-2]>[O:17]=[C:5]1[C:6]2[C:11](=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[C:2]([CH3:13])([CH3:1])[CH2:3][CH2:4]1

参加物

6

反応物 2

HCID 3776IsopropanolHCID 2263961,1,7-Trimethyl-1,2,3,4-tetrahydronaphthalene

生成物 1

HCID 134632674,4,6-Trimethyl-1,2,3,4-tetrahydronaphthalen-1-one

試薬・触媒・溶媒 3

HCID 10219390chromium (VI) trioxide触媒HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒

実験手順

A solution of chromium(VI)oxide (86 g, 0.861 mol) in acetic acid (400 mL) and water (40 mL) was added dropwise to a stirred solution of 1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalene in acetic acid (70 mL) and the reaction mixture stirred 2.5 hours at room temperature. Isopropanol (5 mL) was added and the whole concentrated in vacuo. The residue was dissolved in hexane and filtered over celite. The organic was washed with water and brine, dried (Mg2SO4), filtered and evaporated to give 40.3 g of 1-oxo-4,4,6-trimethyl-1,2,3,4-tetrahydronaphthalene and used without further purification in the bromination (step e). 1H NMR (300 MHz; CDCl3): 1.36 (s, 6 H), 1.98 (t, J=6.9 Hz, 2 H), 2.38 (s, 3 H), 2.68 (t, J=6.9 Hz, 2 H), 7.01 (dd, J1=0.6 Hz, J2=7.9 Hz, 1 H), 7.19 (d, J=0.6 Hz, 1 H), 7.90 (d, J=8.1 Hz, 1 H).

後処理

  1. concentrationthe whole concentrated in vacuo
  2. dissolutionThe residue was dissolved in hexane
  3. filtrationfiltered over celite
  4. washThe organic was washed with water and brine
  5. dry with materialdried (Mg2SO4)
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-11e0bfe9a35f4fc2ae2fb760a3fc6a06
出典データセット
uspto-grants-2007_09
特許番号
US07265139B2

関連ノート

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