Reaction #2389077

Reaction equation

hydrochloric acid

2-acetyl-5-bromo-6-methoxynaphthalene

n-butyl acetate

sodium methoxide

→

product

4-(5-Bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

Solvents

water

Conditions

Workup

1. 1
   Otherequipped with refrigerator and stirrer
2. 2
   workup.ADDITIONare added
3. 3
   Othergoes up to 25° C.
4. 4
   TemperatureThe reaction mixture is then cooled to 0°÷5° C.
5. 5
   workup.WAITkept at this temperature for one hour
6. 6
   FiltrationThe solid is filtered
7. 7
   Washabundantly washed with water on the filter
8. 8
   Washwashed with butyl acetate
9. 9
   Otherdried in oven under vacuum

Procedure

50 Grams (0.179 moles) of 2-acetyl-5-bromo-6-methoxynaphthalene and 200 ml of n-butyl acetate are placed in a flask equipped with refrigerator and stirrer and, under stirring and at the temperature of 15° C., 14.5 g (0.268 moles) of sodium methoxide are added. The temperature of the reaction mixture goes up to 25° C. and is kept at this value for 30 minutes, then the mixture is warmed at 65° C. for one hour, is added with 100 ml of water and is brought to pH 4 by adding a concentrated aqueous solution of hydrochloric acid. The reaction mixture is then cooled to 0°÷5° C. and kept at this temperature for one hour. The solid is filtered, abundantly washed with water on the filter, then washed with butyl acetate and dried in oven under vacuum obtaining 53 g of product with a yield equal to 92%.

Source