4-Chlororesorcinol → 2-(5-Chloro-2,4-dihydroxybenzoyl)benzoic acid

HRID 1372822Notes

Reaction equation

HRID 1372822 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1(=[O:15])[O:10][C:8](=[O:9])[C:7]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:6]12.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([OH:21])=[CH:19][C:18]=1[OH:24]>[N+](C1C=CC=CC=1)([O-])=O>[C:8]([C:7]1[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=1[C:5](=[O:15])[C:22]1[CH:23]=[C:17]([Cl:16])[C:18]([OH:24])=[CH:19][C:20]=1[OH:21])([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 17314-ChlororesorcinolHCID 6811Phthalic AnhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 222233452-(5-Chloro-2,4-dihydroxybenzoyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

AlCl3 (40.0 g, 300 mmol) was added to a solution of phthalic anhydride (20.0 g, 135 mmol) and 4-chlororesorcinol (18.8 g, 130 mmol) in 225 ml nitrobenzene and purged with N2. After stirring overnight, the solution was poured into a vigorously stirred biphasic solution of 750 ml hexanes and 1.0 L 0.5 M aqueous HCl. The solution was allowed to stir for 2 h and the light tan precipitate that formed was filtered and washed with 200 ml aqueous 0.1 M HCl and 300 ml hexanes. The crude product was crystallized from hot MeOH/H2O (12.1 g, 32%). 1H NMR (CD3OD) δ 6.48 (1H, s), 6.95 (1H, s), 7.39 (1H, dd, J 7.2 1.5), 7.62–7.52 (2H, m), 8.12 (1H, dd, J=1.2, 7.8).

Workup

  1. custompurged with N2
  2. additionthe solution was poured into a vigorously stirred biphasic solution of 750 ml hexanes and 1.0 L 0.5 M aqueous HCl
  3. stirringto stir for 2 h
  4. customthe light tan precipitate that formed
  5. filtrationwas filtered
  6. washwashed with 200 ml aqueous 0.1 M HCl and 300 ml hexanes
  7. customThe crude product was crystallized from hot MeOH/H2O (12.1 g, 32%)

Sources & evidence

ORD record
ord-2b69fa3df96849cca376db9d7e0984e3
Source dataset
uspto-grants-2007_01
Patent number
US07160732B2

Reaction notes

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