1,4-Dihydroxy-2-naphthoic acid → 1-Hydroxy-4-benzoylmethoxy-2-naphthoic acid

HRID 972164Notes

Reaction equation

HRID 972164 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]=1[C:13]([OH:15])=[O:14].[OH-].[Na+].[CH2:18](Br)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20]>CN(C=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:18][C:19](=[O:20])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:4][C:3]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 6711,4-Dihydroxy-2-naphthoic acidHCID 6259Phenacyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 214060071-Hydroxy-4-benzoylmethoxy-2-naphthoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

Into a solution of 0.05 mole of 1,4-dihydroxy-2-naphthoic acid in 70 ml. of DMF were dropped, with introduction of nitrogen gas, 10 ml. of a 40% aqueous sodium hydroxide solution and then a solution of 0.05 mole of phenacyl bromide in 10 ml. of DMF, and the resulting mixture was reacted with stirring at 40° C. for 3 to 4 hours. After completion of the reaction, the reaction liquid was poured into ice-hydrochloric acid to deposit crystals, which were then recovered by filtration and recrystallized from acetonitrile to obtain 1-hydroxy-4-benzoylmethoxy-2-naphthoic acid having having a melting point of 190° C. 0.01 Mole of the thus obtained compound and 0.01 mole of N-(δ-2,4-di-tert-amylphenoxy)butylamine were dissolved in 60 ml. of dehydrated dioxane and added with 0.01 mole of dicyclohexyl carbodiimide. The resulting mixture was reacted with stirring at room temperature for 2 hours. After completion of the reaction, the reaction liquid was subjected to filtration, and the filtrate was vaporized under reduced pressure. The residue was charged with n-hexane to deposit crystals, which werethen recoveredby filtration and recrystallized from benzene-n-hexane to obtain a compound having a melting point of 120° to 121° C. (yield 75%). From the measurement of its elementary analysis values and the like, the thus obtained compound was found to be the coupler (1).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. filtrationwere then recovered by filtration
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-3adfee4a53ef44eb991651be1135095a
Source dataset
uspto-grants-1977_10
Patent number
US04052212

Reaction notes

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