Phenol → HCID 20337459, compound

HRID 1706260Notes

Reaction equation

HRID 1706260 reaction equation
BrC(C1C=CC=CC=1)CC.[Mg].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[C:22](O)([CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:23].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(O)C=CC=CC=1>CCOCC>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[CH:22]([CH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH3:23]

Participants

7

Reactant 5

HCID 996PhenolHCID 6101p-Toluenesulfonic acidHCID 562384(1-Bromopropyl)benzeneHCID 5462224MagnesiumHCID 20337442HCID 20337442, compound

Product 1

HCID 20337459HCID 20337459, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 1-bromopropylbenzene (51.7 g., 0.26 mole) in ether (225 ml.) is added dropwise over a one 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 2,5-dimethoxy-acetophenone (50 g.) in ether (60 ml.) is added dropwise and heated to reflux for 1.5 hours. The reaction is quenched by addition of saturated ammonium chloride (250 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 80.3 g. (100%) of 2-(2'5'-dimethyloxyphenyl)-5-phenyl-2-pentanol as an oil. The oil (78.1 g., 0.26 mole), 21.7 g. of p-toluenesulfonic acid and 1250 ml. of phenol are combined and heated at reflux for one hour, while collecting the water (5.5 ml.) evolved in a Dean-Stark apparatus. The mixture is cooled to room temperature, washed with 200 ml. portions of water, saturated sodium bicarbonate and brine, then dried over magnesium sulfate. The filtered phenol layer yields 75.6 g. of 2-(2',5'-dimethoxyphenyl)-5-phenyl-2-pentene as an orange oil upon evaporation.

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 (250 ml.) the ether layer
  5. customis 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 80.3 g
  10. temperatureheated
  11. temperatureat reflux for one hour
  12. customwhile collecting the water (5.5 ml.)
  13. washwashed with 200 ml
  14. dry with materialportions of water, saturated sodium bicarbonate and brine, then dried over magnesium sulfate

Sources & evidence

ORD record
ord-32a4365279d644a7aefd6069a6752fa8
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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