3-Hydroxy-2-naphthoic acid → 2-Naphthalenecarboxylic acid, 4-chloro-3-hydroxy-

HRID 46947

Reaction equation

HRID 46947 reaction equation
[Cl:1][O-].[Na+].[OH:4][C:5]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1>Cl>[Cl:1][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[C:14]([C:15]([OH:17])=[O:16])[C:5]=1[OH:4]

Participants

4

Reactant 2

HCID 71043-Hydroxy-2-naphthoic acidHCID 23665760Sodium Hypochlorite2×

Product 1

HCID 925992-Naphthalenecarboxylic acid, 4-chloro-3-hydroxy-Yield 91.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The chilled sodium hypochlorite solution is added to the chilled solution of 2-hydroxy-3-naphthoic acid, keeping the temperature below 10° C. When the addition of sodium hypochlorite is completed, the reaction mixture is held at about 10° C. for 2 hours and then heated to the boil. To this solution is then added 250 ml of 14.1% hydrochloric acid. The resulting slurry of deep yellow solid material is heated to the boil and then cooled to ambient temperature. The slurry is filtered, washed with 2 liters of water and dried to constant weight. There is obtained 52.6 grams of 1-chloro-2-hydroxy-3-naphthoic acid (purity 97.2% by HPLC) representing a yield of 91.8% of theoretical.

Workup

  1. customthe temperature below 10° C
  2. temperatureheated to the boil
  3. temperatureThe resulting slurry of deep yellow solid material is heated to the boil
  4. filtrationThe slurry is filtered
  5. washwashed with 2 liters of water
  6. customdried to constant weight

Sources & evidence

ORD record
ord-e7a3069927da47618005dcc98e0799b6
Source dataset
uspto-grants-1979_11
Patent number
US04175208

Linked notes

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