Thionyl Chloride → 3-(2,6-Dimethylphenyl)benzyl chloride

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12]O.S(Cl)([Cl:19])=O.O.C(=O)(O)[O-].[Na+]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][Cl:19]

Participants

Procedure

To 3-(2,6-dimethylphenyl)benzyl alcohol (51.9 g) synthesized according to a method described in [WO 2004/041266 pamphlet, (Reference Example 200)], thionyl chloride (130 mL) was gradually added and the resultant reaction mixture was heated under reflux for 3 hours. The reaction mixture was gradually dropped into ice-cooled methanol (inside temperature: 15° C. or less) and the resultant reaction mixture was adjusted to around pH 8 with saturated sodium bicarbonate water, followed by extracting the reaction mixture with ethyl acetate. The resultant organic phase was washed sequentially with a saturated aqueous sodium bicarbonate, water, and saturated saline, and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluate: n-hexane:ethyl acetate=70:1) to obtain the subject compound (36.1 g) as a colorless oil.