2-Methylbenzoxazole → Benzoxazole

HRID 1723531Notes

Reaction equation

HRID 1723531 reaction equation
C[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[Na+]>CS(C)=O>[O:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[CH:2]1

Participants

4

Reactant 2

HCID 72252-MethylbenzoxazoleHCID 14798Sodium Hydroxide

Product 1

HCID 9228BenzoxazoleYield 196.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of this product (8.0 g, 35 mmol) and 2-methylbenzoxazole (4.5 ml, 35 mmol) in DMSO (35 ml) was added a 50% aqueous sodium hydroxide solution (15 ml) and worked up as in Example 8 to give (E)-2-[2-(3,5-dimethyl)-4-chloropropoxyphenyl)ethenyl]benzoxazole as a solid (8.2 g, 70% yield). 1H NMR (CDCl3): δ 7.81-6.88 (m, 8H), 4.01 (t, 2H), 3.66 (t, 2H), 2.31 (s, 6H), 2.00 (m, 2H).

Sources & evidence

ORD record
ord-f9d6bba8590b480693289f587ca0320e
Source dataset
uspto-grants-1989_08
Patent number
US04861897

Reaction notes

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