Benzyl Chloride → Benzyl 2-naphthyl ether

HRID 1707409Notes

Reaction equation

HRID 1707409 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 86632-NaphtholHCID 11430Potassium Carbonate

Product 1

HCID 123080Benzyl 2-naphthyl etherYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

28.2 g (200 mmol) of β-naphthol and 30.4 g (220 mmol) of potassium carbonate were mixed in 80 ml of dimethylformamide, 27.8 g (220 mmol) of benzyl chloride were added dropwise, and the mixture was heated at 120° C. for 2 hours. The residue formed was filtered off, and the filtrate was admixed with water to the onset of cloudiness. Filtration of the cold mixture and drying of the solid gave 44.6 g (95%) of β-naphthyl benzyl ether; melting point: 101° C.

Workup

  1. customThe residue formed
  2. filtrationwas filtered off
  3. filtrationFiltration of the cold mixture
  4. customdrying of the solid

Sources & evidence

ORD record
ord-6f43e8597f184c498f14e5a532b1a87d
Source dataset
uspto-grants-1994_10
Patent number
US05352843

Reaction notes

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