m,alpha-Dichlorotoluene → 5-(m-Chlorobenzyloxy)-2-pyridinemethanol

HRID 443434Notes

Reaction equation

HRID 443434 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][OH:10])=[N:7][CH:8]=1.[Na].[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Cl>CO>[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][OH:10])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 12103m,alpha-DichlorotolueneHCID 5360545SodiumHCID 187584236-(Hydroxymethyl)pyridin-3-ol hydrochloride

Product 1

HCID 234671675-(m-Chlorobenzyloxy)-2-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The solution of 16.2 g of 5-hydroxy-2-pyridinemethanol hydrochloride in 150 ml of methaol is added to a solution of 4.6 g of sodium in 250 ml of methanol, while stirring, over a period of 25 minutes. The solution is stirred for one hour and then a solution of 19.3 g of m-chlorobenzyl chloride in 50 ml of methanol is added. Then the mixture is refluxed for 19 hours, cooled, filtered and the filtrate evaporated to a residue. The residue is suspended in 100 ml of water, made basic with 20% aqueous sodium hydroxide solution and then extracted with chloroform. The chloroform extract is separated, dried over sodium sulfate, filtered and the filtrate evaporated, to yield 5-(m-chlorobenzyloxy)-2-pyridinemethanol melting at 78°-80°.

Workup

  1. stirringThe solution is stirred for one hour
  2. temperatureThen the mixture is refluxed for 19 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe filtrate evaporated to a residue
  6. extractionextracted with chloroform
  7. extractionThe chloroform extract
  8. customis separated
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customthe filtrate evaporated

Sources & evidence

ORD record
ord-664c549644df454194d948c9d7af61de
Source dataset
uspto-grants-1981_04
Patent number
US04260620

Reaction notes

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