4-Hydroxybenzoic Acid → 2-(4-Carboxyphenoxy)benzoic acid

HRID 726772Notes

Reaction equation

HRID 726772 reaction equation
[Na][Na].[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.I[C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([O-:18])=[O:17].[Na+].COCCOCCN(CCOCCOC)CCOCCOC>CN1CCCC1=O.[Cu]Cl>[C:8]([C:7]1[CH:11]=[CH:12][C:4]([O:3][C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=[CH:5][CH:6]=1)([OH:10])=[O:9]

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 141233DisodiumHCID 23666723Benzoic acid, o-iodo-, sodium salt

Product 1

HCID 226650732-(4-Carboxyphenoxy)benzoic acidYield 58%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 40 g (0.22 mol) of the disodium salt of 4-hydroxybenzoic acid, 54 g (0.2 mol) of sodium 2-iodobenzoate, 1.98 g (0.02 mol) of copper(I) chloride and 6.47 g (0.02 mol) of tris-[2-(2-methoxyethoxy)-ethyl]amine (TDA) in 500 ml of N-methylpyrrolidone is kept at 180° C. for 4 hours. The solvent is then removed by distillation, the residue is diluted with about 1 litre of water and thchloric acid. The product w concentrated hydrochloric acid. The product which has precipitated is filtered off and dried under a high vacuum. 29.7 g (58%) of 2-(4-carboxyphenoxy)benzoic acid, melting point 220°-223° C., result as a brown powder.

Workup

  1. customThe solvent is then removed by distillation
  2. additionthe residue is diluted with about 1 litre of water and thchloric acid
  3. customThe product which has precipitated
  4. filtrationis filtered off
  5. customdried under a high vacuum

Sources & evidence

ORD record
ord-42d9b102699c402e896cd096f36b35d6
Source dataset
uspto-grants-1998_01
Patent number
US05710198

Reaction notes

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