Thionyl Chloride → 2,6-Dimethyl-4-isopropylbenzyl chloride

HRID 1003980Notes

Reaction equation

HRID 1003980 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[CH:11]=[C:10]([CH3:17])[C:7]=1[CH2:8]O>C1C=CC=CC=1.O>[CH3:5][C:6]1[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[CH:11]=[C:10]([CH3:17])[C:7]=1[CH2:8][Cl:3]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 154807012,6-Dimethyl4-isopropylbenzyl alcohol

Product 1

HCID 152542812,6-Dimethyl-4-isopropylbenzyl chlorideYield 98.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Thionyl chloride (0.63 g, 5.28 mmol) was added to a solution of 2,6-dimethyl-4-isopropylbenzyl alcohol (Example 2a) (0.47 g, 2.64 mmol) in dry benzene (20 mL). The reaction mixture was allowed to stir at room temperature for 2 hours. The solvent was removed under reduced pressure to give a yellow oil. The crude oil was suspended in water (10 mL) and extracted with ether (3×10 mL). The solvent was removed under reduced pressure to give 0.51 g (98%) of the title compound as a white liquid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give a yellow oil
  3. extractionextracted with ether (3×10 mL)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-58ef71fc2ad34622a8d97fd3abf9fcd5
Source dataset
uspto-grants-2000_04
Patent number
US06048862

Reaction notes

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