Thionyl Chloride → 4-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

HRID 1836419Notes

Reaction equation

HRID 1836419 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]O)=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[Cl:3][CH2:23][C:22]1[CH:25]=[CH:26][C:19]([O:18][CH2:17][C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:10][C:6]=2[CH3:5])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 110228074-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

Product 1

HCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (1.85 ml) was added to a solution of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylalcohol (5.00 g) in toluene (40 ml) and the mixture was stirred at room temperature for 30 minutes. Ice water was added to the reaction mixture followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried over MgSO4 and concentrated to give crystals (5.23 g; yield: 99%) of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole. Recrystallization from ethyl acetate-hexane gave colorless crystals. Melting point: 108-109° C.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ca4dfe52981848c399611513264442a1
Source dataset
uspto-grants-2004_08
Patent number
US06777435B1

Reaction notes

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