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

HRID 2299700Notes

Reaction equation

HRID 2299700 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]O)=[CH:17][CH:16]=1.S(Cl)([Cl:25])=O>C1(C)C=CC=CC=1>[Cl:25][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([O:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])=[CH:16][CH:17]=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

To a solution of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylalcohol (5.00 g) in toluene (40 ml), thionyl chloride (1.85 ml) was added and the mixture was stirred for 30 minutes at room temperature. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated to obtain 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (5.23 g, yield 99%) as crystals. Recrystallization from ethyl acetate-hexane gave colorless crystals. m.p. 108-109° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-18c9ea6fce9f4f559280fe26d3bd8791
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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