4-Hydroxybenzyl Alcohol → HCID 86719586, compound

HRID 922600Notes

Reaction equation

HRID 922600 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[OH:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11]O)=[CH:9][CH:8]=1.[I:15][CH3:16].[K+].[Br-]>>[I-:15].[OH:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][N:1]2[CH:5]=[CH:4][N+:3]([CH3:16])=[CH:2]2)=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 795ImidazoleHCID 6328Methyl iodideHCID 253877Potassium Bromide

Product 1

HCID 86719586HCID 86719586, compound

Conditions

Temperature
155 °C

Procedure

Imidazole (0.1 mol) and 4-hydroxybenzyl alcohol (0.1 mol) were combined and heated to 155° C. The crude product was washed with cold ethanol and recrystallized in an EtOH/DMF mixture. This powder (3-(4-hydroxybenzyl)imidazole, 2.20 mmol) was then was dissolved in DMF (3 mL). Iodomethane (3.21 mmol) was added to the reaction mixture and refluxed for 24 hours at 80° C. The solvent was evaporated and remaining oil was washed using ethyl ether to yield a brown precipitate. Yield: 0.573 g, 82.2%. Mp: 82.9-85.5° C. FTIR: (KBr, cm−1) u(Ar) 1327.37, 1378.80, 1459.39, 1506.20, 1587.78; u(OH) 2922.97. 1H NMR (300 MHz, DMSO-d6) 3.836 (3H, s, CH3N), 5.265 (2H, s, NCH2Ar), 6.796 (2H, d, NCHCHN), 7.275 (2H, d, NCAr), 7.729 (2H, d, HOAr), 9.122 (1H, s, OH), 9.627 (1H, s, NHN).

Workup

  1. washThe crude product was washed with cold ethanol
  2. customrecrystallized in an EtOH/DMF mixture
  3. dissolutionThis powder (3-(4-hydroxybenzyl)imidazole, 2.20 mmol) was then was dissolved in DMF (3 mL)
  4. temperaturerefluxed for 24 hours at 80° C
  5. customThe solvent was evaporated
  6. washwas washed
  7. customto yield a brown precipitate

Sources & evidence

ORD record
ord-9ef673860f3949858dd6540bc7d79d6c
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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