2-Naphthol → 1-Chloro-2-naphthol

HRID 1400244Notes

Reaction equation

HRID 1400244 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[OH:19]>C(Cl)Cl.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[Cl:1][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[OH:19]

Participants

5

Reactant 2

HCID 86632-NaphtholHCID 31398Chlorosuccinimide

Product 1

HCID 124591-Chloro-2-naphtholYield 78%

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 6344DichloromethaneSolvent

Procedure

To a cooled (0-5° C.) solution of N-chlorosuccinimide (1.4 g, 10.4 mmol) in 100 mL of CH2Cl2, ZrCl4 (0.122 g, 5% mol) was added followed by 1.5 g (10.4 mmol) of naphthalen-2-ol. The mixture was stirred for 18 h at room temperature until the complete disappearance of the starting material as judged by TLC and GC analysis. The mixture was quenched with saturated NH4Cl aqueous solution (30 mL) and transferred to a separatory funnel. The two phases were separated and the organic one was washed with water (3×10 mL), dried over Na2SO4 and evaporated under vacuum to give yellow oil. The crude was purified by flash cromatography (petroleum ether/ethyl acetate 85:15) to afford 1-chloronaphtalen-2-ol (1.4 gr, 78% yield), as white solid.

Workup

  1. additionwas added
  2. customThe mixture was quenched with saturated NH4Cl aqueous solution (30 mL)
  3. customtransferred to a separatory funnel
  4. customThe two phases were separated
  5. washthe organic one was washed with water (3×10 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated under vacuum
  8. customto give yellow oil
  9. customThe crude was purified by flash cromatography (petroleum ether/ethyl acetate 85:15)

Sources & evidence

ORD record
ord-638d46fccecb4ce5b042495f27d42097
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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