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

HRID 1889294Notes

Reaction equation

HRID 1889294 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 6212ChloroformSolvent2×

Procedure

To a suspension of 30.0 g 1-Hydroxy-naphthalene-2-carboxylic acid in 600 ml chloroform a mixture of 14.9 ml sulfuryl chloride and 20 ml chloroform was added dropwise. After stirring the reaction for 8 h at room temperature the precipitated product was isolated by filtration, washed with dichloromethane and recrystallized from isopropanol/water to yield 25.1 g of 4-chloro-1-hydroxy-naphthalene-2-carboxylic acid as off-white solid.

Workup

  1. additionwas added dropwise
  2. customthe reaction for 8 h at room temperature the precipitated product
  3. customwas isolated by filtration
  4. washwashed with dichloromethane
  5. customrecrystallized from isopropanol/water

Sources & evidence

ORD record
ord-9e62b52340e64b38871feec2a704d66a
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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