Reaction #465936

Reaction equation

1-Phenyl-2-methoxycarbonyl-4-acetoxy-6,7-dimethoxynaphthalene

sodium hydroxide

→

1-phenyl-4-hydroxy-6,7-dimethoxy-2-naphthoic acid

Yield 100.7%

Solvents

methanol

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux for 3 hours
3. 3
   OtherA white precipitate formed
4. 4
   Filtrationwas collected by vacuum filtration
5. 5
   Washwashed with water
6. 6
   Otherwas air-dried
7. 7
   OtherRecrystallization from ethanol (95 weight percent)

Procedure

1-Phenyl-2-methoxycarbonyl-4-acetoxy-6,7-dimethoxynaphthalene (66.4 grams) from Step 3, 500 mL of a 10 weight percent aqueous sodium hydroxide solution and 50 mL of methanol were added to a reaction flask and heated to reflux for 3 hours and then cooled to room temperature. The reaction mixture was poured onto an aqueous solution of 4N hydrochloric acid/ice mixture (˜400 mL). A white precipitate formed and was collected by vacuum filtration, washed with water and was air-dried. Recrystallization from ethanol (95 weight percent) gave 57 grams of 1-phenyl-4-hydroxy-6,7-dimethoxy-2-naphthoic acid.

Source