Carbon Dioxide → 6-Hydroxy-2-naphthoic acid

HRID 67195

Reaction equation

HRID 67195 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[OH-].[K+].[C:14](=O)([O-:16])[O-:15].[K+].[K+].[C:20](=[O:22])=[O:21]>>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:14]([OH:16])=[O:15])[CH:6]=[CH:5]2.[OH:1][C:2]1[C:11]([C:20]([OH:22])=[O:21])=[CH:10][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 86632-NaphtholHCID 11430Potassium CarbonateHCID 14797Potassium Hydroxide

Product 2

HCID 71043-Hydroxy-2-naphthoic acidHCID 855576-Hydroxy-2-naphthoic acidYield 48.1%

Procedure

The procedure of Example 1 is followed in every detail except that a mixture of 2-hydroxynaphthalene (83 grams; 0.576 mole), 45% potassium hydroxide (69.7 grams; 0.559 mole), and potassium carbonate (20 grams; 0.145 mole) is employed initially, the dehydrated reaction mixture is heated under 60 psi of carbon dioxide for 10 hours, and the aqueous phase is washed twice with 100-ml portions of isopropylnaphthalene at 85°-95° C. There is obtained 25.5 grams of 6-hydroxy-2-naphthoic acid (48.1% of theoretical), and 4.6 grams of 3-hydroxy-2-naphthoic acid.

Workup

  1. washthe aqueous phase is washed twice with 100-ml portions of isopropylnaphthalene at 85°-95° C

Sources & evidence

ORD record
ord-926691553479479691a22abababa8562
Source dataset
uspto-grants-1982_08
Patent number
US04345095

Linked notes

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