Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: P(Cl)(Cl)([Cl:3])=O.CN([CH:9]=[O:10])C.[C:11]1(=O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1.C([O-])(=O)C.[Na+]>ClC=C(Cl)Cl>[Cl:3][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][C:12]=1[CH:9]=[O:10]
Reactant: O=C1CCCc2ccccc21
Reactant: CN(C)C=O
Reactant: O=P(Cl)(Cl)Cl
Agent: CC(=O)[O-]
Agent: [Na+]
Solvent: ClC=C(Cl)Cl
Product: O=CC1=C(Cl)c2ccccc2CC1
Temperature: 60 °C
Reaction time: 8 h
Yield: 94.7 %

Procedure:
Phosphorus oxychloride (25.82 mL, 0.277 mol) was added dropwise to a solution of trichloroethylene (62.5 mL) and DMF (25.48 mL, 0.329 mol) keeping the temperature between 5°-10° C. -Tetralone (40 g, 0.274 mol) in trichloroethylene (62.5 mL) was added dropwise. The reaction mixture was stirred at 60° C. for 3 hours and at room temperature overnight. An aqueous sodium acetate solution (100 g/300 mL H2O) was added dropwise while cooling in a water bath. The aqueous phase was extracted with ether (3×200 mL), dried (MgSO4) and concentrated to give an oil (50 g). 20 g of this crude oil was chromatographed on silica gel with 50% ethyl acetate/hexane to yield 9.95 g (50%) of pure product as a white solid, m.p. 37° C.