Ethyl Acetate → 1-Chloro-6-methoxy-2-naphthalenol

HRID 1771474Notes

Reaction equation

HRID 1771474 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:13])[CH:7]=[CH:6]2.C1C(=O)N([Cl:21])C(=O)C1.CCOC(C)=O>CN(C=O)C>[Cl:21][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[OH:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 2886346-Methoxy-2-naphthol

Product 1

HCID 128080931-Chloro-6-methoxy-2-naphthalenolYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6-methoxynaphthalen-2-ol (1.00 g, 5.74 mmol) in DMF (15 mL) was added NCS (843 mg, 6.31 mmol). The reaction mixture was stirred at 25° C. for 16 hours. Diluted the reaction with EtOAc, washed with H2O and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification by silica gel column (PE/EtOAc=100/1) gave the product (940 mg, yield 87%).

Workup

  1. additionDiluted
  2. washwashed with H2O and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel column (PE/EtOAc=100/1)

Sources & evidence

ORD record
ord-55e8f21f33e04d399b1086e6ab92c621
Source dataset
uspto-grants-2016_02
Patent number
US09249132B2

Reaction notes

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