Thionyl Chloride → 1-(1-Chloroethyl)naphthalene

HRID 1886527

Reaction equation

HRID 1886527 reaction equation
[C:1]1([CH:11](O)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[C:1]1([CH:11]([Cl:16])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 980301-(1-Naphthyl)ethanol

Product 1

HCID 132442811-(1-Chloroethyl)naphthalene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(1-naphthalyl)ethanol (6.34 g, 38.8 mmol) and thionyl chloride (5.37 ml, 73.6 mmol) in 65 ml of toluene was refluxed for 4 hours. The reaction mixture was evaporated to give the residue as an oil. The residue was dissolved in 150 ml of ethyl acetate, washed successively with 50 ml of water, 50 ml of saturated sodium bicarbonate and 50 ml of brine, and dried over sodium sulfate. The solvent was removed in vacuo to give 3(6.83 g, 97%) as an oil.

Workup

  1. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-aeeee3d783ad454c8ab37aa78190e494
Source dataset
uspto-grants-1992_09
Patent number
US05151526

Linked notes

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