Diethyl Ether → HCID 18987251, compound

HRID 2396520Notes

Reaction equation

HRID 2396520 reaction equation
O1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]1([Mg]Br)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:15]1[CH:16]=[C:17]([O:22][CH3:23])[CH:18]=[C:19](Cl)[CH:20]=1.[Cl-].[NH4+].[CH2:26](OCC)[CH3:27]>Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:6]1([C:15]2[CH:16]=[C:17]([O:22][CH3:23])[CH:18]=[C:19]([C:2]3[CH:27]=[CH:26][CH:5]=[CH:4][CH:3]=3)[CH:20]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 365883,5-DichloroanisoleHCID 178418255HCID 178418255, compound

Product 1

HCID 18987251HCID 18987251, compound

Reagents, catalysts & solvents 1

HCID 178418751HCID 178418751, compoundCatalyst

Procedure

To a mixture of 150 cc of tetrahydrofuran and 34 cc of a 3M solution of phenylmagnesium bromide in diethylether at 40° C. under an argon athmosphere, are added 15 g of 3,5-dichloroanisole and 5.5 g of bis(triphenylphosphine)nickel(II) chloride. The resultant black mixture is heated for 6 hours to 65° C. and then poured into 400 cc of a saturated aqueous solution of ammonium chloride. After extraction with ethyl acetate (3×150 cc), the combined organic extracts are washed with water, dried (MgSO4) and concentrated in vacuo. The resultant residue is flash chromatographed on silica gel (30-60 mm; eluent: 20:0.1 n-hexane/ethyl acetate) and recristallized from 20 cc of methanol to give 3,5-diphenyl-anisole as a white solid. (m.p.=93°-94° C.)

Workup

  1. temperatureThe resultant black mixture is heated for 6 hours to 65° C.
  2. extractionAfter extraction with ethyl acetate (3×150 cc)
  3. washthe combined organic extracts are washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel (30-60 mm; eluent: 20:0.1 n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2ce1dcb91530486e9a9af7dcca47456d
Source dataset
uspto-grants-1996_02
Patent number
US05492915

Reaction notes

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