1-Hydroxy-2-naphthoic acid → 4-Chloro-1-hydroxy-2-naphthoic acid

HRID 274763Notes

Reaction equation

HRID 274763 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:13].S(Cl)([Cl:18])(=O)=O>C(Cl)(Cl)Cl>[Cl:18][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[C:3]([C:12]([OH:14])=[O:13])[CH:4]=1

Participants

4

Reactant 2

HCID 68441-Hydroxy-2-naphthoic acidHCID 24648Sulfuryl chloride

Product 1

HCID 794164-Chloro-1-hydroxy-2-naphthoic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 1-hydroxy-2-naphthoic acid (3.76 g; 0.02 m) in chloroform (50 ml) was added sulphuryl chloride (2.97 g; 0.022 m) dropwise and the solution stirred at room temperature for two hours. The solvent was removed in vacuo to give a white solid which was washed with water, collected and dried. The crude solid was recrystallised from ethanol to give 4-chloro-1-hydroxy-naphthalene-2-carboxylic acid as white needles.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a white solid which
  3. washwas washed with water
  4. customcollected
  5. customdried
  6. customThe crude solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-99c0744a252342369b1fee01e7c5e924
Source dataset
uspto-grants-1995_02
Patent number
US05389684

Reaction notes

Loading…