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

HRID 915177

반응식

HRID 915177 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 10219390chromium (VI) trioxide촉매HCID 176Acetic Acid용매2회HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-11e0bfe9a35f4fc2ae2fb760a3fc6a06
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265139B2

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