1,1,7-Trimethyl-1,2,3,4-tetrahydronaphthalene → 4,4,6-Trimethyl-1,2,3,4-tetrahydronaphthalen-1-one

HRID 51161

반응식

HRID 51161 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.Br([O-])(=O)=[O:15].[K+].[N+]([O-])([O-])=O.[NH4+].[Ce]>O.O1CCOCC1.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[C:5](=[O:15])[CH2:4][CH2:3]1

참가 물질

7

반응물 3

HCID 2263961,1,7-Trimethyl-1,2,3,4-tetrahydronaphthaleneHCID 23673461Potassium BromateHCID 57418452Ammonium cerium-nitrate

생성물 1

HCID 134632674,4,6-Trimethyl-1,2,3,4-tetrahydronaphthalen-1-one수율 89%

시약·촉매·용매 3

HCID 962Water용매2회HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
0 °C

실험 절차

A solution of 1,2,3,4-tetrahydro-1,1,7-trimethyl-naphthalene (9.60 g, 55 mmol), potassium bromate (9.17 g, 55 mmol), cerium ammonium nitrate (1.50 g) in water (28 mL) and dioxane (44 mL) was heated under argon at 85° C. for 6 hours. The mixture was then cooled to 0° C., diluted with ethyl acetate and water. The organic phase was separated and the aqueous phase extracted with ethyl acetate. The combined organic extracts were washed with water (2×), saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (6.5×17 cm, 10% ethyl acetate/hexane) to give the title material (9.2 g, 89%) as a colorless oil.

후처리

  1. customThe organic phase was separated
  2. extractionthe aqueous phase extracted with ethyl acetate
  3. washThe combined organic extracts were washed with water (2×), saturated sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (6.5×17 cm, 10% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-5a6a05f22504482d946a9a88e8cb4b00
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713515B2

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