Potassium Carbonate → HCID 14800667, compound

HRID 729019Notes

Reaction equation

HRID 729019 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.Cl[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[CH2:20][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12][CH3:13])=[O:11])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 14800666HCID 14800666, compound

Product 1

HCID 14800667HCID 14800667, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 3-(4-hydroxybenzyl)benzoate (0.08 mol), 2-chloromethylquinoline (0.10 mol) and potassium carbonate (anhydrous, 0.10 mol) are heated at reflux in a 7:1 mixture of acetone:dimethylformamide (600 ml) until all the benzoate starting material is consumed. The reaction is then filtered, evaporated and the residue diluted with water and extracted with ethyl acetate. The ethyl acetate extracts are dried (magnesium sulfate), evaporated and then applied to a silica gel column. Elution with ethyl acetate:petroleum ethergives methyl 3-(4-(2-quinolinylmethyloxy)benzyl)benzoate.

Workup

  1. temperatureare heated
  2. customdimethylformamide (600 ml) until all the benzoate starting material is consumed
  3. filtrationThe reaction is then filtered
  4. customevaporated
  5. additionthe residue diluted with water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe ethyl acetate extracts are dried (magnesium sulfate)
  8. customevaporated
  9. washElution with ethyl acetate

Sources & evidence

ORD record
ord-0e71cca9ff3e4e689baf22887e279adf
Source dataset
uspto-grants-1991_09
Patent number
US05051427

Reaction notes

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