ChemicalBook CAS DataBase List 6-METHOXY-5-(TRIFLUOROMETHYL)-1-NAPHTHOIC ACID

6-METHOXY-5-(TRIFLUOROMETHYL)-1-NAPHTHOIC ACID synthesis

7synthesis methods

Product Name:6-METHOXY-5-(TRIFLUOROMETHYL)-1-NAPHTHOIC ACID
CAS Number:84532-72-9
Molecular formula:C13H9F3O3
Molecular Weight:270.2

Naphthalene, 2-methoxy-5-methyl-1-(trifluoromethyl)-

85674-78-8
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6-METHOXY-5-(TRIFLUOROMETHYL)-1-NAPHTHOIC ACID

84532-72-9
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Yield:84532-72-9 55%

Reaction Conditions:

with sodium hydroxide;potassium permanganate in water;tert-butyl alcohol;

Steps:

8 Procedure A

EXAMPLE 8 6-Methoxy-5-(trifluoromethyl)-1-naphthalenecarboxylic acid (VIII, R=CH₃) Procedure A A solution of KMnO₄ (1.58 g, 10 mmol) in water (15 mL) was added dropwise over a period of 6 hr to a refluxing solution of 2-methoxy-5-methyl-1-(trifluoromethyl)naphthalene (500 mg, 2.1 mmol) in water/tert-butanol (11.8:88.2; 10 mL). The mixture was heated at reflux for an additional one hour and, while still hot, the mixture was filtered. The solid, collected on the filter, was washed with hot water and ethyl acetate. The combined filtrate and washings were concentrated under reduced pressure to a volume of about 3 mL. Water (20 mL) and 0.5 N aqueous NaOH (10 mL) were added to the residue. The mixture was extracted with diethyl ether. After drying (MgSO₄) and evaporating of the extract, 140 mg of starting material was obtained. The aqueous layer from the preceding extraction was rendered acidic with 1 N aqueous H₂ SO₄. The resulting precipitate was collected, washed on the filter with water and dried over P₂ O₅ under reduced pressure for 18 hr to give the title compound (222 mg, 55% yield based on recovered starting material). The product had mp 221°-222° C.

References:

US4408077,1983,A