4-Nitrophenol → 1,4-Benzenedicarboxylic acid, bis(4-nitrophenyl) ester

HRID 703612Notes

Reaction equation

HRID 703612 reaction equation
[OH-:1].[Na+].[CH:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[C:5]([OH:12])[CH:4]=1.[C:13](Cl)(=[O:23])[C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>O.C(Cl)Cl>[N+:9]([C:8]1[CH:7]=[CH:6][C:5]([O:12][C:13](=[O:23])[C:14]2[CH:22]=[CH:21][C:17]([C:18]([O:1][C:5]3[CH:4]=[CH:3][C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=3)=[O:19])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1)([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 7488Terephthaloyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 81455211,4-Benzenedicarboxylic acid, bis(4-nitrophenyl) ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A 300-ml r.b. flask, equipped with a magnetic stirring bar was charged with 7.85 g sodium hydroxide (Fisher, 0.197 moles) in 75 ml of deionized water and then, to the stirred solution, 27.40 g of p-nitrophenol (Aldrich, 98%, 0.197 moles) was added. The solution turned orange and a considerable amount of yellow solid was present. A solution of 20.04 g of terephthaloyl chloride (Aldrich, 97%, 0.0987 moles assuming 100% purity) in methylene chloride was dripped into the flask from a dropping funnel. The flask was stirred another 15 min and the mixture filtered through a Whatman's #1 filter paper disk on a Buchner funnel. The filtrate was almost clear and the solid on the filter was washed with a few portions of water in the funnel and with two small portions of acetone. The solid was dried by briefly drawing air through it in a vacuum funnel and then, broken into finer pieces, in a 65° C. vacuum oven. The crude product weighed 36.1 g (theory, 40.2 g) and melted at 228°-243° C.

Workup

  1. customflask, equipped with a magnetic stirring bar
  2. filtrationthe mixture filtered through a Whatman's #1
  3. filtrationfilter paper disk on a Buchner funnel
  4. washthe solid on the filter was washed with a few portions of water in the funnel and with two small portions of acetone
  5. customThe solid was dried
  6. custombroken into finer pieces, in a 65° C.

Sources & evidence

ORD record
ord-e04c375656e44edf877e6dbef94f7bf1
Source dataset
uspto-grants-1991_01
Patent number
US04983679

Reaction notes

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