6-Hydroxy-2-naphthoic acid → HCID 68547060, compound

HRID 2241789Notes

Reaction equation

HRID 2241789 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.[OH:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21](O)[CH:22]=2)[CH:17]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>S(=O)(=O)(O)O.C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][C:22]1[C:23]3[C:18](=[CH:17][C:16]([OH:15])=[CH:25][CH:24]=3)[CH:19]=[CH:20][CH:21]=1)=[O:13])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 855576-Hydroxy-2-naphthoic acidHCID 935522,6-DihydroxynaphthaleneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 68547060HCID 68547060, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalyst2×HCID 1140TolueneSolvent

Procedure

A mixture of 9.41 g (0.05 mol) of 6-hydroxy-2-naphthoic acid, 24.03 g (0.15 mol) of 2,6-dihydroxynaphthalene, 0.8 g of p-toluenesulfonic acid monohydrate and 3 drops of concentrated sulfuric acid in 100 ml of toluene was heated under reflux with occasional addition of concentrated sulfuric acid (3 drops every 3 h) for 12 h. The resulting suspension was cooled to room temperature and filtered. The filtercake was suspended in methanol, the suspension was stirred for 3 h and the solid was finally filtered off. 10.9 g of 6-hydroxynaphthyl 6-hydroxy-2-naphthoate (“NpNp”) were obtained as a brownish solid which was processed in the subsequent step without further purification.

Workup

  1. temperaturewas heated
  2. filtrationfiltered
  3. filtrationthe solid was finally filtered off

Sources & evidence

ORD record
ord-ab29793590cb4ac1a17e36fc4e8b1ab6
Source dataset
uspto-grants-2010_03
Patent number
US07670505B2

Reaction notes

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