Sodium → HCID 54488544, compound

HRID 1289059Notes

Reaction equation

HRID 1289059 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15].[Na]>C(=O)(OC)OC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]([C:14]([O:16][CH3:17])=[O:15])[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 14620154Methyl 2-(3-methoxyphenoxy)phenylacetate

Product 1

HCID 54488544HCID 54488544, compound

Reagents, catalysts & solvents 1

HCID 12021Dimethyl CarbonateSolvent

Procedure

Methyl 2-(3-methoxyphenoxy)phenylacetate (6.81 g) was dissolved in 11 mL of dimethyl carbonate and 600 mg of sodium was added. The mixture was heated at reflux for 10 h, then cooled. The reaction mixture was quenched with water, acidified with concentrated aqueous HCl and extracted with dichloromethane. The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure to give an oil. The desired material was separated from unreacted starting material by flash chromatography (4:1 hexane: ethyl acetate as eluant) to yield after concentration, 3.54 g (43%) of the title compound of Step B. 1H NMR (CDCl3): δ7.46(dd,J=1.5,7.5Hz,1H), 7.29 (t,J=8Hz,1H), 7.2 (m,2H), 6.92 (d,J=8Hz,1H), 6.65 (td, J=1.5,7.5Hz,1H), 6.5 (m,2H), 5.14 (s,1H), 3.77 (s,3H), 3.73 (s,6H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 10 h
  3. temperaturecooled
  4. customThe reaction mixture was quenched with water
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give an oil
  10. customThe desired material was separated
  11. customto yield
  12. concentrationafter concentration, 3.54 g (43%) of the title compound of Step B

Sources & evidence

ORD record
ord-dffc1669862a402dbdc6dbd3f939f6b9
Source dataset
uspto-grants-1998_05
Patent number
US05747516

Reaction notes

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