(+/-)-2-(6-METHOXY-2-NAPHTHYL)PROPIONIC ACID synthesis
- Product Name:(+/-)-2-(6-METHOXY-2-NAPHTHYL)PROPIONIC ACID
- CAS Number:23981-80-8
- Molecular formula:C14H14O3
- Molecular Weight:230.26
2700-47-2
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Yield:23981-80-8 80%
Reaction Conditions:
with potassium hydroxide;iodine in methanol;water
Steps:
1.b Preparation of dl 2-(6'-methoxy-2'-naphthyl)-propionic acid:
(b) To a solution of trimethylorthoformate (14.4 ml; 0.14 mole) in methanol (40 ml; 0.99 mole) was added 0.1 ml of a 48% solution of hydrochloric in methanol and the 1-(6'-methoxy-2'-naphthyl)-1-propanone (10 g; 0.047 mole). After 10 minutes the solution became homogeneous and was maintained under reflux for 2 hours. It was then cooled to 40° C. and iodine (11.85 g; 0.047 mole) was added. The reaction mixture was refluxed for 30 hours, the solvent was removed by distillation and the residue was treated with potassium hydroxide in methanol (0.20 mole in 40 ml) at boiling for 2 hours. The reaction mixture was evaporated to dryness, dissolved in water and extracted with ethyl ether. The aqueous layer was acidified to precipitate the dl 2-(6'-methoxy-2'-naphthyl)-propionic acid weighing (after drying) 8.65 g; m.p. 154°-155° C. (yield, 80%).
References:
BLASCHIM S.p.A. US4608441, 1986, A
201230-82-2
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