Toluene → 4-(3-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole

HRID 584374Notes

Reaction equation

HRID 584374 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:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]O.C1(C)C=CC=CC=1>O>[Cl:3][CH2:22][C:21]1[CH:20]=[C:19]([CH:26]=[CH:25][CH:24]=1)[O:18][CH2:17][C:7]1[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:10][C:6]=1[CH3:5]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 11140977{3-[(5-Methyl-2-Phenyl-1,3-Oxazol-4-Yl)methoxy]phenyl}methanol

Product 1

HCID 108815514-(3-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazoleYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Thionyl chloride (4.45 ml) was added dropwise to a mixture of 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylalcohol (15.0 g) and toluene (200 ml) at 0° C. After stirring at room temperature for 1 hour, water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate-hexane to obtain 4-(3-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (13.4 g, yield 84%) as pale-yellow crystals. m.p. 79-80° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe remaining crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b74414dc63b54fcbac438dc3fea7e587
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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