Pyridinium chloride → 2-(3-Hydroxyphenyl)-5-phenylpentane

HRID 261349Notes

Reaction equation

HRID 261349 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16]C=2)[CH:6]=[CH:7][CH:8]=1.Cl.N1C=CC=C[CH:22]=1>Cl.O>[OH:2][C:3]1[CH:4]=[C:5]([CH:9]([CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:22])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 10176127Pyridinium chlorideHCID 86736615HCID 86736615, compound

Product 1

HCID 204968222-(3-Hydroxyphenyl)-5-phenylpentane

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 2-(3-methoxyphenyl-5-phenylpentane (20 g.) and pyridine hydrochloride (94 g.) under nitrogen is heated to 190° C. for 2 hours with vigorous stirring. The reaction mixture is cooled, dissolved in 6 N hydrochloric acid (200 ml.) and diluted with water to 600 ml. The aqueous solution is extracted with ethyl acetate (4×100 ml.), the ethyl acetate extracts dried over sodium sulfate and concentrated under vaccum to yield the crude product which is purified by silica gel chromatography to yield 2-(3-hydroxyphenyl)-5-phenylpentane as an oil.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionThe aqueous solution is extracted with ethyl acetate (4×100 ml.)
  3. dry with materialthe ethyl acetate extracts dried over sodium sulfate
  4. concentrationconcentrated under vaccum
  5. customto yield the crude product which
  6. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-acf74f4d1ba144aa86f38712be3f27ef
Source dataset
uspto-grants-1979_08
Patent number
US04165323

Reaction notes

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