Carbon Dioxide → 3-Hydroxy-2-naphthoic acid

HRID 868703Notes

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[O-:11].[Na+].C1C2C(=CC=CC=2)C=CC=1O.[C:24](=[O:26])=[O:25].S(=O)(=O)(O)O>O>[OH:11][C:2]1[C:3]([C:24]([OH:26])=[O:25])=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

Conditions

Temperature: 40 °C

Procedure

In a pressure reaction vessel were charged 166 g of sodium 2-naphtholate, 72 g of 2-naphthol and 498 g of hydrogenated triphenyl, and a reaction was allowed to proceed at 260° C. and at a carbon dioxide pressure of 5 kg/cm2 (G) for 3 hours, with stirring. The reaction mixture was charged into 800 ml of water, and the resulting mixture was adjusted to a pH 5.5 with sulfuric acid, followed by separation into the reaction medium layer and the water layer at 85° C. The 2-naphthol was recovered with an aqueous sodium hydroxide solution from the reaction medium layer. After recovery of 2-naphthol, the water layer was adjusted to a pH 2.0 with sulfuric acid at the same temperature, cooled to 40° C. and subjected to filtration to give 89.3 g of 2-hydroxynaphthalene-3-carboxylic acid. The product was found to contain only 0.1% of 2-hydroxynaphthalene-6-carboxylic acid, with no trace of 2-hydroxynaphthalene- 1-carboxylic acid. The yield based on sodium 2-naphtholate was 47.5%, with the selectivity being 99.3%.

Workup

customIn a pressure reaction vessel
customfollowed by separation into the reaction medium layer
customat 85° C
customThe 2-naphthol was recovered with an aqueous sodium hydroxide solution from the reaction medium layer
filtrationsubjected to filtration

Sources & evidence

ORD record: ord-22190a8c8ac54a2195921f446023ecb5
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04780567

Reaction notes

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