Sulfuric Acid → Isopropyl benzenesulfonate

HRID 428574Notes

Reaction equation

HRID 428574 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CCOCC1.[CH:18]([OH:21])([CH3:20])[CH3:19].S(=O)(=O)(O)O>C(OC)(C)(C)C>[C:1]1([S:7]([O:21][CH:18]([CH3:20])[CH3:19])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 7369Benzenesulfonyl chlorideHCID 79724-Methylmorpholine

Product 1

HCID 12441430Isopropyl benzenesulfonate

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Benzenesulfonyl chloride (50 g, 283 mmol) was added to a solution of 4-methylmorpholine (57 g, 2 equiv.) and isopropyl alcohol (66 g, 3.9 equiv.). After reaction completion (ca. 3 hours), 250 mL of methyl tert-butyl ether (MTBE) and 60 mL of 3M sulfuric acid were added. The rich MTBE layer was washed with aqueous sodium chloride solution. The rich MTBE solution was solvent exchanged into tetrahydrofuran solution. The rich tetrahydrofuran solution containing 56 g (96 M %, HPLC area % 97) of the title compound was used as is in the next step (Example 5).

Workup

  1. additionwere added
  2. washThe rich MTBE layer was washed with aqueous sodium chloride solution
  3. additionThe rich tetrahydrofuran solution containing 56 g (96 M %, HPLC area % 97) of the title compound

Sources & evidence

ORD record
ord-c0bf0411337a4fa1b9eee3dd18ad2e4c
Source dataset
uspto-grants-2001_11
Patent number
US06313308B1

Reaction notes

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