Potassium Hydroxide → 4-Methoxy-3-nitrobenzoic acid

HRID 1517Notes

Reaction equation

HRID 1517 reaction equation
[N+:1]([C:4]1[C:5](C)=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7]([O-:9])=[O:8])([O-:3])=[O:2].[OH-].[K+]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7]([OH:9])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 189170523-Nitro-4-methoxy-methylbenzoate

Product 1

HCID 666404-Methoxy-3-nitrobenzoic acidYield 76.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. filtrationafter which the resulting solid was collected by vacuum filtration
  2. washwashed with 2×100 ml of ethyl ether
  3. dissolutionThe solid was dissolved in 200 ml of water
  4. filtrationThe resulting precipitate was collected by vacuum filtration
  5. washwashed with 200 ml water
  6. customdried overnight in vacuo at 30° C

Sources & evidence

ORD record
ord-275e8400c15942e28e2a52018fda7f14
Source dataset
uspto-grants-1998_03
Patent number
US05726162

Reaction notes

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