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

HRID 444359Notes

Reaction equation

HRID 444359 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 (18.4 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 vacuum to yield the crude product. The product is purified by silica gel chromatography.

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

Sources & evidence

ORD record
ord-059ada7efebb4f87a3a7fb3c68cccf34
Source dataset
uspto-grants-1981_04
Patent number
US04263438

Reaction notes

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