Reaction #1613

Reaction equation

3-nitro-4-methoxy-methylbenzoate

potassium hydroxide

→

product

Yield 76.6%

3-nitro-4-methoxy benzoic acid

Yield 76.6%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Filtrationafter which the resulting solid was collected by vacuum filtration
2. 2
   Washwashed with 2×100 ml of ethyl ether
3. 3
   workup.DISSOLUTIONThe solid was dissolved in 200 ml of water
4. 4
   FiltrationThe resulting precipitate was collected by vacuum filtration
5. 5
   Washwashed with 200 ml water
6. 6
   Otherdried overnight in vacuo at 30° C

Procedure

To a 500 ml erlenmeyer flask with magnetic stirrer was charged 10.3 g of 3-nitro-4-methoxy-methylbenzoate, 400 ml tetrahydrofuran, and 3.2 g of 86% potassium hydroxide. The reaction was stirred for 12 hours at ambient temperature, after which the resulting solid was collected by vacuum filtration and washed with 2×100 ml of ethyl ether. The solid was dissolved in 200 ml of water and acidified to pH 4 with 6N hydrochloric acid. The resulting precipitate was collected by vacuum filtration, washed with 200 ml water, and dried overnight in vacuo at 30° C. Isolated 7.4 g of product as a white solid.

Source