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

HRID 346028Notes

Reaction equation

HRID 346028 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24601Cesium iodideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-247c94125d3645308c0867241150d39c
Source dataset
uspto-grants-1991_10
Patent number
US05059609

Reaction notes

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