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

HRID 1111761Notes

Reaction equation

HRID 1111761 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:10])[CH:6]=[CH:7][CH:8]=1.Cl.N1C=CC=CC=1>Cl.O>[OH:2][C:3]1[CH:4]=[C:5]([CH:9]([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:10])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 10176127Pyridinium chlorideHCID 204968262-(3-Methoxyphenyl)-5-phenylpentane

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 6N 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 vacuum 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 vacuum
  5. customto yield the crude product which
  6. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-a7b313d1986b4e7ba10e5b61b7a43759
Source dataset
uspto-grants-1978_10
Patent number
US04118559

Reaction notes

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