ChemicalBook CAS DataBase List 2-PHENYLBENZO[D]OXAZOLE-6-CARBOXYLIC ACID

2-PHENYLBENZO[D]OXAZOLE-6-CARBOXYLIC ACID synthesis

5synthesis methods

Product Name:2-PHENYLBENZO[D]OXAZOLE-6-CARBOXYLIC ACID
CAS Number:594839-90-4
Molecular formula:C14H9NO3
Molecular Weight:239.23

6-Benzoxazolecarboxylic acid, 2-phenyl-, methyl ester

136663-22-4
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2-PHENYLBENZO[D]OXAZOLE-6-CARBOXYLIC ACID

594839-90-4
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Yield:594839-90-4 6.0 g

Reaction Conditions:

Stage #1: methyl 2-phenylbenzo[d]oxazole-6-carboxylatewith sodium hydroxide in water;acetonitrile at 50; for 20 h;
Stage #2: in water;acetonitrile;Acidic conditions;Further stages;

Steps:

6.A A. 2-Phenylbenzo[d]oxazole-6-carboxylic acid, 6c

A solution of methyl 4-amino-3-hydroxybenzoate 6a (29.9 mmol, 5.0 g) and benzaldehyde 6b (29.9 mmol, 3.02 mL) in 150 mL of MeOH was stirred at 20° C. for 3 h.
The solvent was removed under vacuum and the residue was mixed with 150 mL of acetonitrile.
Lead (IV) acetate (29.9 mmol, 13.3 g) was added in one portion and the mixture was refluxed for 20 min.
After cooling, the precipitate was removed by filtration and washed with acetonitrile.
The filtrate and wash solutions were stirred with 3N aqueous NaOH (120 mmol, 40 mL) at 50° C. for 20 h.
After cooling, the reaction mixture was acidified and filtered to give 6.0 g (79%) of compound 6c. MS m/z 240.0 (M+H⁺).

References:

US2013/102584,2013,A1 Location in patent:Paragraph 0318; 0319

2374-03-0 Synthesis