Hydrochloric Acid → Phenyl 4-chloro-1-hydroxy-2-naphthoate

HRID 1262973Notes

Reaction equation

HRID 1262973 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19].Cl>C(OCC)(=O)C.O.C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 117874-Chloro-1-naphtholHCID 15891Phenyl chloroformateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 118936Phenyl 4-chloro-1-hydroxy-2-naphthoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

To a 500-mL, three-neck, nitrogen-purged flask was added 17.9 g (0.10 mole) of 4-chloro-1-naphthol, 100 mL of methylene chloride, 15 g (0.11 mole) of anhydrous aluminum chloride, and 15 mL (0.12 mole) of phenyl chloroformate. This mixture was heated to reflux. After 48 hours, the mixture was cooled to 10° C. and 200 mL of water and 15 mL of 37% hydrochloric acid were added. To this mixture was added 100 mL of ethyl acetate. The layers were separated and the organic layer was washed with two 100-mL portions of 5N hydrochloric acid. The organic layer was dried with anhydrous magnesium sulfate, filtered, then the solvent stripped off under vacuum. The resulting oil solidified and the crude product was recrystallized from isopropyl alcohol. The yield of phenyl 4-chloro-1-hydroxy-2-naphthoate (off-white, m.p. 102°-104° C.) obtained was 54%.

Workup

  1. customTo a 500-mL, three-neck, nitrogen-purged flask
  2. temperatureThis mixture was heated to reflux
  3. customThe layers were separated
  4. washthe organic layer was washed with two 100-mL portions of 5N hydrochloric acid
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe crude product was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-3dab23d8e42f4e00aa2a3f52ab657744
Source dataset
uspto-grants-1984_06
Patent number
US04454340

Reaction notes

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