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

HRID 1595451Notes

Reaction equation

HRID 1595451 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 20 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-17b686a1b9334e4590b5786724bf2e24
Source dataset
uspto-grants-2001_09
Patent number
US06288101B1

Reaction notes

Loading…