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

HRID 445105Notes

Reaction equation

HRID 445105 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

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 230827203-(2,6-Dimethylphenyl)benzyl alcoholHCID 86585896Sodium bicarbonate water

Product 1

HCID 679729603-(2,6-Dimethylphenyl)benzyl chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. additionwas gradually added
  2. customthe resultant reaction mixture
  3. temperaturewas heated
  4. temperatureunder reflux for 3 hours
  5. additionThe reaction mixture was gradually dropped into ice-
  6. customthe resultant reaction mixture
  7. extractionby extracting the reaction mixture with ethyl acetate
  8. washThe resultant organic phase was washed sequentially with a saturated aqueous sodium bicarbonate, water, and saturated saline
  9. dry with materialwas dried over anhydrous sodium sulfate
  10. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
  11. customthe resultant residue was purified by silica gel column chromatography (eluate: n-hexane:ethyl acetate=70:1)

Sources & evidence

ORD record
ord-2cc495937e164a29b5adc101cac9f1fc
Source dataset
uspto-grants-2013_07
Patent number
US08476287B2

Reaction notes

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