Phenol → 3,4-Dihydro-7-methoxy-2-phenoxy-1(2H)-naphthalenone

HRID 346028

반응식

HRID 346028 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:15]1[CH2:24][CH2:23][C:22]2[C:17](=[CH:18][C:19]([O:25][CH3:26])=[CH:20][CH:21]=2)[C:16]1=[O:27]>CC(C)=O.[I-].[Cs+]>[CH3:26][O:25][C:19]1[CH:18]=[C:17]2[C:22]([CH2:23][CH2:24][CH:15]([O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:16]2=[O:27])=[CH:21][CH:20]=1

참가 물질

6

반응물 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 3119062-Bromo-3,4-dihydro-7-methoxy-1(2H)-naphthalenone

생성물 1

HCID 196006623,4-Dihydro-7-methoxy-2-phenoxy-1(2H)-naphthalenone수율 61%

시약·촉매·용매 2

HCID 24601Cesium iodide촉매HCID 180Acetone용매

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온도
0 °C

실험 절차

A mixture of 2.95 g (31.4 mmol) of phenol, 25.5 g (78.2 mmol) of cesium carbonate and 320 mg (1.23 mmol) of cesium iodide in 64 ml of acetone was heated at reflux for 40 minutes and then cooled to 0° C. To this 0° C. mixture was added 8.00 g (31.4 mmol) of 2-bromo-3,4-dihydro-7-methoxy-1(2H)-naphthalenone. The resultant reaction mixture was stirred 3 hours at 0° C. and 15 hours at 25° C., then filtrated. The filtrate was evaporated to an oil which was purified via column chromatography on 400 g of silica gel, eluting with 25% ether-hexane, to give 5.14 g (61%) of present title product as an oil, crystallized from ether-hexane, m.p. 94.5°-96.5° C.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 40 minutes
  3. customThe resultant reaction mixture
  4. filtrationfiltrated
  5. customThe filtrate was evaporated to an oil which
  6. customwas purified via column chromatography on 400 g of silica gel
  7. washeluting with 25% ether-hexane

출처 및 근거

ORD 기록
ord-247c94125d3645308c0867241150d39c
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05059609

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