Acetone → Methyl 6-hydroxy-2-naphthoate

HRID 365010Notes

Reaction equation

HRID 365010 reaction equation
O(C([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[CH:12]=2)[CH:7]=1)(C)C)O.CC(C)=[O:22]>S(=O)(=O)(O)O>[OH:22][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[CH:12]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 13628560HCID 13628560, compound

Product 1

HCID 390995Methyl 6-hydroxy-2-naphthoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

In the case where 1.0 g of the present compound, methyl 2-(2-hydroperoxy-2-propyl)naphthalene-6-carboxylate are heated in 10.0 g of acetone for 30 min at a temperature between 50° and 70° C. in the presence of 0.02 g of sulfuric acid as a catalyst, methyl 2-hydroxynaphthalene-6-carboxylate is formed nearly quantitatively. The thus formed compound is hydrolyzed nearly quantitatively into 2-hydroxynaphthalene-6-carboxylic acid (acid-6) by heating the thus formed compound for 30 min at a temperature between 20° and 50° C. in an aqueous about 1N alkali solution.

Sources & evidence

ORD record
ord-b54158b7340041b1bfebcc30897205e8
Source dataset
uspto-grants-1986_08
Patent number
US04607117

Reaction notes

Loading…