Benzene → Methyl(1-hydroxy-2-methyl-6-methoxy-indenyl)acetate

HRID 263615노트

반응식

HRID 263615 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH:8]([CH3:13])[C:9]2=[O:12])=[CH:5][CH:4]=1.Br[CH2:15][C:16]([O:18][CH3:19])=[O:17].C1C=CC=CC=1.II>C(O)(=O)C.C(O)C.CCOCC>[CH3:19][O:18][C:16](=[O:17])[CH2:15][C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:9]([OH:12])[C:8]=1[CH3:13]

참가 물질

8

반응물 4

HCID 241Benzene2회HCID 807IodineHCID 60984Methyl bromoacetateHCID 2311786-Methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 131718936Methyl(1-hydroxy-2-methyl-6-methoxy-indenyl)acetate

시약·촉매·용매 3

HCID 176Acetic Acid용매2회HCID 702Ethanol용매HCID 3283Diethyl Ether용매

실험 절차

A solution of 13.4 g. of 6-methoxy-2-methylindanone and 19.3 g. of methyl bromoacetate in 45 ml. benzene is added over a period of 5 minutes to 21 g. of zinc amalgam (prepared according to Org. Syn. Coll., vol. 3) in 110 ml. benzene and 40 ml. dry ether. A few crystals of iodine are added to start the reaction, and the reaction mixture is maintained at reflux temperature (ca. 65°) with external heating. At three hour intervals, two batches of 10 g. zinc amalgam and 10 g. bromoester are added, and the mixture is then refluxed for eight hours. After addition of 30 ml. ethanol and 150 ml. of acetic acid, the mixture is poured into 700 ml. of 1:1 aqueous acetic acid. The organic layer is separated, and the aqueous layer is extracted twice with ether. The combined organic layers are washed thoroughly with water, ammonium hydroxide and water. Drying over sodium sulfate, evaporation of solvent in vacuo followed by pumping at 80° (bath temp.) (1-2 mm.) gives crude methyl(1-hydroxy-2-methyl-6-methoxy-indenyl)acetate.

후처리

  1. customthe reaction
  2. temperaturethe reaction mixture is maintained
  3. temperatureat reflux temperature (ca. 65°) with external heating
  4. temperaturethe mixture is then refluxed for eight hours
  5. additionAfter addition of 30 ml
  6. customThe organic layer is separated
  7. extractionthe aqueous layer is extracted twice with ether
  8. washThe combined organic layers are washed thoroughly with water, ammonium hydroxide and water
  9. dry with materialDrying over sodium sulfate, evaporation of solvent in vacuo
  10. customby pumping at 80°

출처 및 근거

ORD 기록
ord-98c2847997d14e9399fc51afe34a057b
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05643959

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