Diphenyl Ether → Ethyl 5-oxo-5-(4-phenoxyphenyl)pentanoate

HRID 847364Notes

Reaction equation

HRID 847364 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:6]([O:8][C:9](=[O:16])[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)[CH3:7].[C:17]1([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.C(Cl)Cl>ClC(Cl)C>[CH2:6]([O:8][C:9](=[O:16])[CH2:10][CH2:11][CH2:12][C:13](=[O:15])[C:27]1[CH:28]=[CH:29][C:24]([O:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:25][CH:26]=1)[CH3:7]

Participants

6

Reactant 4

HCID 7583Diphenyl EtherHCID 6451240Aluminum(III) ChlorideHCID 21908982Water methylene chlorideHCID 53445130HCID 53445130, compound

Product 1

HCID 13584387Ethyl 5-oxo-5-(4-phenoxyphenyl)pentanoate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

93 g aluminium chloride are added over 15 minutes at -10° C. to a solution of 52.0 g glutaric acid monoethyl ester chloride [Cl--CO--(CH2)3 --COOC2H5 ]. The mixture is stirred for 15 mins. at 0° to 10° C. and then added portion-wise over a period of 20 mins. at -5° to 10° C. to a pre-prepared solution of 50.0 g diphenylether in 150 ml dichloroethane. The reaction mixture is allowed to rise slowly to room temperature and is then stirred for 12 hours, poured onto ice and shaken well with H2O/methylene chloride. The organic phase is washed thouroughly with H2O and saturated NaHCO3 solution, dried over MgSO4 and the solvent evaporated off. The obtained light yellow oil is crystallised from hexane/ethyl ether on an ice bath: m.p.=61°-62° C.

Workup

  1. additionat 0° to 10° C. and then added portion-wise over a period of 20 mins
  2. customat -5° to 10° C.
  3. customto rise slowly to room temperature
  4. stirringis then stirred for 12 hours
  5. additionpoured onto ice
  6. washThe organic phase is washed thouroughly with H2O and saturated NaHCO3 solution
  7. dry with materialdried over MgSO4
  8. customthe solvent evaporated off
  9. customThe obtained light yellow oil
  10. customis crystallised from hexane/ethyl ether on an ice bath

Sources & evidence

ORD record
ord-dcc6e8aa03984b469353f90d6bf8c6d7
Source dataset
uspto-grants-1992_08
Patent number
US05141951

Reaction notes

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