Hydrochloric Acid → 2-(3-Methoxyphenyl)-5-phenylpentane

HRID 1111760Notes

Reaction equation

HRID 1111760 reaction equation
Br[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][CH3:4].[Mg].[CH2:12](O)[CH3:13].Cl.C[CH2:17][O:18][CH2:19][CH3:20]>[Pd]>[CH3:17][O:18][C:19]1[CH:20]=[C:5]([CH:12]([CH2:4][CH2:3][CH2:2][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:13])[CH:2]=[CH:3][CH:4]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3283Diethyl Ether3×HCID 562384(1-Bromopropyl)benzeneHCID 5462224Magnesium

Product 1

HCID 204968262-(3-Methoxyphenyl)-5-phenylpentane

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 1-bromopropylbenzene (51.7 g.) in ether (234 ml.) is added dropwise over a 2-hour period to a refluxing mixture of magnesium (7.32 g.) in ether (78 ml.). The reaction mixture is refluxed for 30 minutes longer and then a solution of 3-methoxy-acetophenone (46.3 g.) in ether (78 ml.) is added dropwise and heated to reflux for 1.5 hours. The reaction is quenched by addition of saturated ammonium chloride (234 ml.), the ether layer is separated and the aqueous phase extracted with ether (3 × 200 ml.). The combined ether extracts are dried over magnesium sulfate and concentrated under vacuum to yield an oil. The oil is hydrogenated in a mixture containing ethanol (600 ml.), concentrated hydrochloric acid (4 ml.) and 5% palladium-on-carbon (10 g.). The catalyst is filtered off and the ethanol removed under vacuum. The residue is distilled under vacuum yielding 2-(3-methoxyphenyl)-5-phenylpentane.

Workup

  1. temperatureThe reaction mixture is refluxed for 30 minutes longer
  2. temperatureheated
  3. temperatureto reflux for 1.5 hours
  4. customThe reaction is quenched by addition of saturated ammonium chloride (234 ml.)
  5. customthe ether layer is separated
  6. extractionthe aqueous phase extracted with ether (3 × 200 ml.)
  7. dry with materialThe combined ether extracts are dried over magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customto yield an oil
  10. filtrationThe catalyst is filtered off
  11. customthe ethanol removed under vacuum
  12. distillationThe residue is distilled under vacuum

Sources & evidence

ORD record
ord-7dfe2c949c4a45ec882c9fe9abe96fda
Source dataset
uspto-grants-1978_10
Patent number
US04118559

Reaction notes

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