1,3,5-Tri-tert-butylbenzene → HCID 12247166, compound

HRID 2387533Notes

Reaction equation

HRID 2387533 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]([C:10]1[CH:15]=[C:14](C(C)(C)C)[CH:13]=[C:12]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=1)([CH3:9])([CH3:8])[CH3:7]>>[C:6]([C:10]1[CH:15]=[C:14]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:13]=[C:12]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 150891,3,5-Tri-tert-butylbenzeneHCID 24638Chlorosulfonic acid

Product 1

HCID 12247166HCID 12247166, compoundYield 50%

Conditions

Temperature
0 °C

Procedure

Chlorosulfonic acid (4 mL) was added to 1,3,5-tri-tert-butyl-benzene (1.5 g, 6.1 mmol) which had been cooled to 0° C. After being stirred at 0° C. for 30 minutes, the mixture was warmed to room temperature and stirred for 1 hour. Then the mixture was poured into ice water (50 mL) and extracted with dichloromethane (20 mL×3). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (gradient elution: 0-20% ethyl acetate in petroleum ether) to afford 3,5-di-tert-butyl-benzenesulfonyl chloride (880 mg, 50%) as a yellow solid (reference: Guthrie, R. D. et al. Aust. J. Chem. 40 (1987) 2133).

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred for 1 hour
  3. extractionextracted with dichloromethane (20 mL×3)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (gradient elution: 0-20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-cfceaaccb0c943a7aab0b96d2d226ebe
Source dataset
uspto-grants-2012_09
Patent number
US08268870B2

Reaction notes

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