Hydrochloric Acid → HCID 14086163, compound

HRID 1900623Notes

Reaction equation

HRID 1900623 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].Cl>CO.O>[C:15]1([CH2:14][CH2:13][CH2:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 22107100HCID 22107100, compound

Product 1

HCID 14086163HCID 14086163, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 4-(4-phenylbutyl)phenyl acetate (8.29 g) in methanol (112 ml) and water (97 ml) was added sodium carbonate (13.10 g). The reaction was refluxed. After 3.5 hours, the reaction mixture was allowed to cool to room temperature. After 25 minutes at room temperature, the reaction mixture was treated with 5N HCl (50 ml). It was then concentrated in vacuo to remove the majority of the methanol present. Diethyl ether (250 ml) was added to the residue, then the material was treated with 1N HCl (3×100 ml) and the phases were separated. The material was dissolved in diethyl ether, then the denied compound was isolated by flash silica-gel filtration, eluting with hexane/ethyl acetate (20:1, 92×13 ml). The fractions containing the denied compound were combined and concentrated in vacuo to give 1.57 g of 4-(4-phenyl butyl)phenol an oil. Upon standing at room temperature the oil crystallized out.

Workup

  1. temperatureThe reaction was refluxed
  2. waitAfter 25 minutes at room temperature
  3. concentrationIt was then concentrated in vacuo
  4. customto remove the majority of the methanol present
  5. additionDiethyl ether (250 ml) was added to the residue
  6. additionthe material was treated with 1N HCl (3×100 ml)
  7. customthe phases were separated
  8. dissolutionThe material was dissolved in diethyl ether
  9. customthe denied compound was isolated by flash silica-gel filtration
  10. washeluting with hexane/ethyl acetate (20:1, 92×13 ml)
  11. additionThe fractions containing the denied compound
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8d770a1055942d7b88902f636a9c511
Source dataset
uspto-grants-1996_11
Patent number
US05576323

Reaction notes

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