Pyridinium chloride → 2-(4-Ethylbenzyl)resorcinol

HRID 2219460Notes

Reaction equation

HRID 2219460 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[C:4]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][CH:13]=1.Cl.N1C=CC=CC=1>O>[CH2:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:4]2[C:3]([OH:2])=[CH:8][CH:7]=[CH:6][C:5]=2[OH:9])=[CH:13][CH:14]=1)[CH3:19]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 230727321,3-Dimethoxy-2-(4-ethylbenzyl)benzene

Product 1

HCID 230727622-(4-Ethylbenzyl)resorcinolYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 1,3-dimethoxy-2-(4-ethylbenzyl)benzene (6.0 g, 23.4 mmol) and pyridine hydrochloride (21.6 g, 187 mmol) was heated and stirred at 180° C. for 15 hours. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic phase was washed with diluted aqueous hydrochloric acid and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate 80:20) to give 2-(4-ethylbenzyl)resorcinol (5.2 g, 97%) as a light-brown oil.

Workup

  1. temperaturewas heated
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with diluted aqueous hydrochloric acid and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate 80:20)

Sources & evidence

ORD record
ord-d0b46b7649c447f686bed27b1335c3d9
Source dataset
uspto-grants-2008_08
Patent number
US07414072B2

Reaction notes

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