1-Hydroxy-2-naphthoic acid → 1-Hydroxynaphthalene-2-carbonyl chloride

HRID 1438833Notes

Reaction equation

HRID 1438833 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=O.S(Cl)([Cl:17])=O>CN(C)C=O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([Cl:17])=[O:14]

Participants

4

Reactant 2

HCID 68441-Hydroxy-2-naphthoic acidHCID 24386Thionyl Chloride

Product 1

HCID 130240501-Hydroxynaphthalene-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dry 1-hydroxy-2-naphthoic acid (50 gms., 0.266 mole) was suspended in 350 ml. dry benzene in a flame-dried 1 liter 1-neck round bottom flask under an air condenser and drying tube. Thionyl chloride (31.7 gms., 0.266 mole) was added in one portion followed by 1.5 ml. dry N,N-dimethylformamide. The reaction mixture was stirred magnetically 2-3 days at room temperature. Insoluble material (6.5 gms.) was removed by filtration, and the yellow-tan filtrate was evaporated to dryness to give pale yellow 1-hydroxy-2-naphthoyl chloride, m.p. 87°-88° C. Chilled anhydrous methanol (100 ml.) was added quickly to the solid chloride in an exothermic reaction. The partial solution was heated about 5 minutes on the steam bath under a drying tube then allowed to cool. The suspension was chilled and the solid was collected to give 43 gms. (92% by weight) of 1-hydroxy-2-methyl naphthoate.

Workup

  1. dry with materialdry benzene in a flame-dried 1 liter 1-neck round bottom flask under an air condenser and drying tube
  2. customInsoluble material (6.5 gms.) was removed by filtration
  3. customthe yellow-tan filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f4a7660537f3450782bb5893fdfb14e3
Source dataset
uspto-grants-1977_11
Patent number
US04056539

Reaction notes

Loading…