Thionyl Chloride → 1-tert-Butyl-4-(chloromethyl)-2-isopropylbenzene

HRID 1675256Notes

Reaction equation

HRID 1675256 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11]O)=[CH:7][C:6]=1[CH:13]([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:18])=O>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][Cl:18])=[CH:7][C:6]=1[CH:13]([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59300613(4-tert-Butyl-3-isopropylphenyl)methanol

Product 1

HCID 593006801-tert-Butyl-4-(chloromethyl)-2-isopropylbenzeneYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alcohol 26.4 (77.0 mg, 0.37 mmol) was dissolved in anhydrous DCM (5.0 mL). Thionyl chloride (0.041 mL, 0.56 mmol) was added dropwise to the above solution. The resulting mixture was stirred at room temperature for 24 hours. The organic solvent was then removed under vacuo to give a white solid (80 mg). The crude product (26.5) was used in the next step without further purification.

Workup

  1. customThe organic solvent was then removed under vacuo

Sources & evidence

ORD record
ord-3550e94759c642fd906a6f7dc7c0103e
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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