Hydrochloric Acid → 4-(2-Phenyl-4-oxazolylmethoxy)benzylalcohol

HRID 350000Notes

Reaction equation

HRID 350000 reaction equation
[BH4-].[Na+].[C:3]1([C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=3)[N:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO.Cl>O>[C:3]1([C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:17]=[CH:18][C:19]([CH2:20][OH:21])=[CH:22][CH:23]=3)[N:13]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 108265134-(2-Phenyl-4-oxazolylmethoxy)benzaldehyde

Product 1

HCID 230248884-(2-Phenyl-4-oxazolylmethoxy)benzylalcoholYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride (0.36 g) was added to a mixture of 4-(2-phenyl-4-oxazolylmethoxy)benzaldehyde (2.65 g) and methanol (50 ml) under ice-cooling, which was stirred at room temperature for 1 hour. Dilute hydrochloric acid and water were added to the reaction mixture, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated to obtain 4-(2-phenyl-4-oxazolylmethoxy)benzyl alcohol (2.43 g, yield 91%) as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 141–142° C.

Workup

  1. temperaturecooling
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-93ce78c37ffa4b52a7cc5359d8df1b12
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

Loading…