4-Methyloxybenzyl chloride → HCID 67303374, compound

HRID 2061607Notes

Reaction equation

HRID 2061607 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][Cl:16])=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Cl-:16].[OH:8][C:7]1[C:2]([CH3:1])=[N+:3]([CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 707192-Methylpyridin-3-ol

Product 1

HCID 67303374HCID 67303374, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 2-methyl-3-hydroxypyridine (71) (10 g, 91.6 mmol) in toluene (45 mL) was added 4-methyoxybenzyl chloride (72) (12.4 mL, 1 eq). The mixture was refluxed overnight. The solvent was concentrated to about ⅓ of the volume. After cooling, the solid was isolated via filtration and washed with a small amount of toluene to give the desired product, which was used without further purification. 1H NMR (d6-DMSO) δ 8.61 (d, 1H, J=6 Hz), 8.16 (d, 1H, J=8.4 Hz), 7.85 (t, 1H, J=6.9 Hz), 7.28 (d, 2H, J=8.1 Hz), 7.02 (d, 2H, J=8.4 Hz), 5.82 (s, 2H), 3.79 (s 3H), 2.59 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationThe solvent was concentrated to about ⅓ of the volume
  3. temperatureAfter cooling
  4. customthe solid was isolated via filtration
  5. washwashed with a small amount of toluene

Sources & evidence

ORD record
ord-6b6272c04f2b48809699bdd25f88dea7
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

Loading…