Tetraethyl orthocarbonate → 2-Ethoxy-6-hydroxybenzoxazole

HRID 468549Notes

Reaction equation

HRID 468549 reaction equation
Cl.[NH2:2][C:3]1[CH:9]=[CH:8][C:6]([OH:7])=[CH:5][C:4]=1[OH:10].C([O-])(=O)C.[Na+].[C:16](OCC)(OCC)(OCC)[O:17][CH2:18][CH3:19]>C(O)C>[CH2:18]([O:17][C:16]1[O:10][C:4]2[CH:5]=[C:6]([OH:7])[CH:8]=[CH:9][C:3]=2[N:2]=1)[CH3:19]

Participants

5

Reactant 3

HCID 66213Tetraethyl orthocarbonateHCID 517045Sodium AcetateHCID 134088224-Aminobenzene-1,3-diol hydrochloride

Product 1

HCID 210777992-Ethoxy-6-hydroxybenzoxazoleYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of equivalent amounts of 4-aminoresorcinol hydrochloride and anhydrous sodium acetate in anhydrous ethanol was stirred for 16 hours at room temperature with a slight excess of tetraethyl orthocarbonate to give 2-ethoxy-6-hydroxybenzoxazole in 60% yield.

Sources & evidence

ORD record
ord-013baac4dbbf4a3bb6ccf774c468cbf3
Source dataset
uspto-grants-2014_01
Patent number
US08624025B2

Reaction notes

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