3-Hydroxybenzyl alcohol → Benzenemethanol, 3-(2-quinolinylmethoxy)-

HRID 892175Notes

Reaction equation

HRID 892175 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[OH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][OH:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][O:14][C:15]1[CH:16]=[C:17]([CH2:18][OH:19])[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 1023-Hydroxybenzyl alcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 14650410Benzenemethanol, 3-(2-quinolinylmethoxy)-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-Chloromethylquinoline hydrochloride (11.6 g, 54 mmol), 3-hydroxybenzyl alcohol (6.7 g, 54 mmol) and potassium carbonate (16 g, 116 mmol) are heated in DMF (45 mL) at 50° C. for 14 h. The temperature is increased to 80° C. and heated an additional 24 h. The reaction is cooled and added to water, filtered and the solid is washed with water to yield a semi-pure product. The residue is dissolved in ethyl acetate, dried over magnesium sulfate, filtered and concentrated. The sample is then recrystallized from ethyl acetate and hexanes to provide the title compound. MS (ESI) 266 (M+H)+.

Workup

  1. temperatureheated an additional 24 h
  2. temperatureThe reaction is cooled
  3. filtrationfiltered
  4. washthe solid is washed with water
  5. customto yield a semi-pure product
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe sample is then recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-81608a03163c4d268cc7fba6c4af8c85
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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