Water → HCID 54173499, compound

HRID 728821Notes

Reaction equation

HRID 728821 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Cl[CH2:16][C:17]([CH3:19])=[CH2:18].O>C1COCC1.C(OCC)C>[CH3:18][C:17](=[CH2:16])[CH2:19][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 823151-(p-Hydroxyphenyl)imidazole

Product 1

HCID 54173499HCID 54173499, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Suspend 40 g (0.25 mol) of 4-(1H-imidazol-1-yl)phenol in 280 mL of THF and treat with 15 9 (0.375 mol) of a 60% dispersion of sodium hydride in mineral oil. Stir this suspension for 20 min and then add 27.1 mL (0.25 mol) of 3-chloro-2-methylpropene. Heat this mixture to 100° C. for 3 h. After this time, add 250 mL of water and 250 mL of diethyl ether and separate the layers. Re-extract the aqueous layer with 2×250 mL of diethyl ether. Evaporate the combined ether extracts on a rotary evaporator. Triturate with 300 mL of hexanes and filter off the resulting solid to provide the title compound.

Workup

  1. customseparate the layers
  2. customEvaporate the combined ether
  3. customextracts on a rotary evaporator
  4. customTriturate with 300 mL of hexanes
  5. filtrationfilter off the resulting solid

Sources & evidence

ORD record
ord-425298c8cec744898583c02fb2364a38
Source dataset
uspto-grants-1991_09
Patent number
US05051423

Reaction notes

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