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

HRID 346028

反応式

HRID 346028 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24601Cesium iodide触媒HCID 180Acetone溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-247c94125d3645308c0867241150d39c
出典データセット
uspto-grants-1991_10
特許番号
US05059609

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