Chlorosulfonic acid → 503470-40-4

HRID 1815438Notes

Reaction equation

HRID 1815438 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[Cl:12][S:13](O)(=[O:15])=[O:14]>C(Cl)(Cl)Cl>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([S:13]([Cl:12])(=[O:15])=[O:14])[CH:6]=2)[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 68110Chromanone

Product 1

HCID 22500934503470-40-4

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-chromanone (0.59 g, 4.0 mmol) in CHCl3 (10 mL) was added chlorosulfonic acid (1.0 mL, 15 mmol) and heated to 40° C. for 1 h. After cooling to rt, the solution was poured onto ice and extracted with CH2Cl2 (10 mL). The organic layer was washed with 1 M HCl (3×10 mL) and the combined organic extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure to afford 4-oxochroman-6-sulfonyl chloride as a grey solid in quantitative yield. 1H NMR (CD3OD) δ 8.41 (s, 1H), 8.05 (d, 1H), 7.13 (d, 1H), 4.7 (t, 2H), 3.0 (t, 2H).

Workup

  1. temperatureAfter cooling to rt
  2. additionthe solution was poured onto ice
  3. extractionextracted with CH2Cl2 (10 mL)
  4. washThe organic layer was washed with 1 M HCl (3×10 mL)
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f9419f41316d44bdb772551067fc84e6
Source dataset
uspto-grants-2005_04
Patent number
US06878743B2

Reaction notes

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