Chlorosulfonic acid → 3-isopropyl-4-methoxybenzenesulfonyl chloride

HRID 352554Notes

Reaction equation

HRID 352554 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11])([CH3:3])[CH3:2].[Cl:12][S:13](O)(=[O:15])=[O:14]>C(Cl)Cl>[Cl:12][S:13]([C:8]1[CH:7]=[CH:6][C:5]([O:10][CH3:11])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:9]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 2706232-Isopropylanisole

Product 1

HCID 227120843-isopropyl-4-methoxybenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-isopropylanisole (0.40 g, 2.66 mmol) in CH2Cl2 (9 mL) cooled with an ice water bath was added slowly chlorosulfonic acid (4 mL). After 1.5 h of cooling, the mixture was poured into a flask containing ice (25 g). The product was extracted with CH2Cl2 (50 mL). The organic extract was washed with brine (25 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford 0.62 g of grayish oil as crude product. The crude product was purified by chromatography using the ISCO Combiflash SQ16x system (0 to 20% EtOAc in hexane, 20 min gradient, 35 g Redisep silica gel column) to give 0.56 g (84%) of compound 50a as a clear oil.

Workup

  1. temperatureAfter 1.5 h of cooling
  2. additionthe mixture was poured into a flask
  3. extractionThe product was extracted with CH2Cl2 (50 mL)
  4. extractionThe organic extract
  5. washwas washed with brine (25 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c5f2fbd40dc460cba103413696a4d0a
Source dataset
uspto-grants-2004_06
Patent number
US06747048B2

Reaction notes

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