2-Naphthol → 3-Hydroxy-2-naphthoic acid

HRID 1414834Notes

Reaction equation

HRID 1414834 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[OH-].[Na+].C1C(N=NC2C(=O)N(C3C=CC(S([O-])(=O)=O)=CC=3)N=C2[C:38]([O-:40])=[O:39])=CC=C(S([O-])(=O)=O)C=1.[Na+].[Na+].[Na+].N(CC(O)=O)(CC(O)=O)CC(O)=O>>[OH:11][C:2]1[C:3]([C:38]([OH:40])=[O:39])=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

5

Reactant 4

HCID 86632-NaphtholHCID 8758Nitrilotriacetic AcidHCID 14798Sodium HydroxideHCID 164825Tartrazine

Product 1

HCID 71043-Hydroxy-2-naphthoic acidYield 73%

Procedure

An autoclave equipped with stirrer is charged with 1,220 parts of β-naphthol, 640 parts of aqueous sodium hydroxide solution (50% strength by weight) and 6 parts of the trisodium salt of nitrilotriacetic acid (dissolved in 15 parts of water). The charge is mixed thoroughly under nitrogen until the internal temperature reaches 260° C. 510 parts of 2-hydroxy-naphthalene-3-carboxylic acid (corresponding to 73% of theory, based on β-naphthol converted) are obtained analogously to Example 1. The proportion of resin formed is 12 mole percent, based on β-naphthol employed. 685 parts of β-naphthol are recovered.

Workup

  1. customAn autoclave equipped with stirrer
  2. additionThe charge is mixed thoroughly under nitrogen until the internal temperature
  3. customreaches 260° C

Sources & evidence

ORD record
ord-de2ea499dc074822814011b821d0fc96
Source dataset
uspto-grants-1977_01
Patent number
US04002675

Reaction notes

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