Hydrochloric Acid → HCID 22458892, compound

HRID 613409Notes

Reaction equation

HRID 613409 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH:23]=[CH2:24].Cl>CN(C=O)C>[CH2:24]([O:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:8][CH:9]=1)[CH:23]=[CH2:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 6414404-(4-Methylphenoxy)phenol

Product 1

HCID 22458892HCID 22458892, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4'-methylphenoxy)phenol (4.75 g, 23.30 mmol), potassium carbonate (4.17 g, 30.30 mmol) and allyl bromide (2.22 mL, 25.60 mmol) in DMF (50 mL) was stirred for 5 h at 60° C. After cooling, the reaction mixture was neutralized with 1 N HCl and extracted with ethyl acetate. The organic extract was washed with brine, dried over sodium sulfate, filtered and concentrated to afford an oil which was chromatographed on silica gel (15% ethyl acetate/hexane) to afford 4-(4'-methylphenoxy)phenyl allyl ether.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford an oil which
  9. customwas chromatographed on silica gel (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-36336ac02806417680bd061711279cae
Source dataset
uspto-grants-1999_12
Patent number
US06008237

Reaction notes

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