Hydrochloric Acid → 5-Styrylresorcinol

HRID 2414705Notes

Reaction equation

HRID 2414705 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[C:7]([O:9]C)[CH:8]=1.Cl.N1C=CC=CC=1.Cl>C(OCC)C>[OH:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[C:7]([OH:9])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2387781,3-Dimethoxy-5-(2-phenylethenyl)benzeneHCID 10176127Pyridinium chloride

Product 1

HCID 1007545-Styrylresorcinol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
165 °C

Procedure

For demethylation, a homogeneous mixture of 54.0 g (0.22 mol) of 3,5-dimethoxystilbene and 40.0 g (0.35 mol) of pyridine hydrochloride is heated at about 165° C. for 3 hours. The cooled, oily reaction mass is then introduced into 1.2 liters of 2N hydrochloric acid and the crude product is isolated by extraction with diethyl ether. Recrystallisation from toluene yields 3,5-dlihydroxystilbene in the form of a pale-yellow powder.

Sources & evidence

ORD record
ord-f57433c302ef4ff3a532caffc32899ab
Source dataset
uspto-grants-2004_11
Patent number
US06814960B1

Reaction notes

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