Potassium Carbonate → Benzenemethanol, 4-chloro-alpha-ethyl-alpha-(4-((6-methyl-2-pyridinyl)methoxy)phenyl)-

HRID 745221

Reaction equation

HRID 745221 reaction equation
[CH2:1]([C:3]([OH:18])([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32]Cl)[N:27]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][O:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)([OH:18])[CH2:1][CH3:2])=[CH:9][CH:8]=2)[N:27]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 765462-(Chloromethyl)-6-methylpyridineHCID 14727318alpha-Ethyl-alpha-(4-chlorophenyl)-4-hydroxy-benzylalcohol

Product 1

HCID 3022025Benzenemethanol, 4-chloro-alpha-ethyl-alpha-(4-((6-methyl-2-pyridinyl)methoxy)phenyl)-

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

13.1 g. of α-ethyl-α-(4-chlorophenyl)-4-hydroxybenzyl-alcohol, 14 g. of anhydrous potassium carbonate, 0.85 g. of tetrabutylammonium hydrogensulfate and 7.8 g. of 2-methyl-6-chloromethyl-pyridine in 140 ml. of ethyl acetate are boiled for 18 hours. The solvent is distilled off under reduced pressure, to the residue water is added, and it is extracted with ether. The ethereal solution is washed to neutral with a 5% aqueous potassium hydroxide solution and subsequently water, dried over anhydrous magnesium sulfate, and evaporated in vacuo. Crystallization of the residue from a mixture of hexane and ethyl acetate yields 13.6 g. of the title compound, melting at 100° to 101° C.

Workup

  1. distillationThe solvent is distilled off under reduced pressure, to the residue water
  2. additionis added
  3. extractionit is extracted with ether
  4. washThe ethereal solution is washed to neutral with a 5% aqueous potassium hydroxide solution and subsequently water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customCrystallization of the residue
  8. additionfrom a mixture of hexane and ethyl acetate
  9. customyields 13.6 g

Sources & evidence

ORD record
ord-2be7deb7c5794779bbdbc1444ceead4d
Source dataset
uspto-grants-1986_07
Patent number
US04598080

Linked notes

Loading…