Benzyl Chloride → 4,5-Dihydro-4-methyl-2-phenyl-4-[(phenylmethoxy)methyl]oxazole

HRID 267901Notes

Reaction equation

HRID 267901 reaction equation
[OH:1][CH2:2][C:3]1([CH3:14])[CH2:7][O:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:4]1.[H-].[Na+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[CH2:17]([O:1][CH2:2][C:3]1([CH3:14])[CH2:7][O:6][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:4]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 226853(4-Methyl-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl)methanol

Product 1

HCID 215527614,5-Dihydro-4-methyl-2-phenyl-4-[(phenylmethoxy)methyl]oxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A suspension of 4-hydroxymethyl-4-methyl-2-phenyloxazoline (19.1 grams, prepared by the method described in J. Amer, Chem. Soc. 1945, 67, 1069) in toluene (200 milliliters) was added slowly to a stirred suspension of sodium hydride (2.4 grams) in toluene (50 milliliters). Some warming was necessary to initiate the reaction. The mixture was then heated under reflux for 2 hours with stirring. Benzyl chloride (13.0 grams) was added to the mixture over a period of 10 minutes. The mixture was heated under reflux for a further 5 hours and then allowed to stand at room temperature for 16 hours. The mixture was washed with water (3 × 200 milliliters), dried (MgSO4) and evaporated under reduced pressure. The residue was distilled in vacuo to give the desired product, boiling point 147°-149°C at 0.3 Torr.

Workup

  1. customprepared by the method
  2. customthe reaction
  3. temperatureThe mixture was then heated
  4. temperatureunder reflux for 2 hours
  5. temperatureThe mixture was heated
  6. temperatureunder reflux for a further 5 hours
  7. washThe mixture was washed with water (3 × 200 milliliters)
  8. dry with materialdried (MgSO4)
  9. customevaporated under reduced pressure
  10. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-62fcc27052124492be4366b777cf5817
Source dataset
uspto-grants-1976_03
Patent number
US03945998

Reaction notes

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