Chlorosulfonic acid → HCID 55279352, compound

HRID 1986617Notes

Reaction equation

HRID 1986617 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH2:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][C:7]1=[O:16]>>[O:16]=[C:7]1[CH2:6][C:15]2[CH:14]=[C:13]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 682662-Tetralone

Product 1

HCID 55279352HCID 55279352, compoundYield 20%

Conditions

Temperature
0 °C

Procedure

To chlorosulfonic acid (4.5 mL, 68 mmol), cooled to 0° C. in an ice-bath, was added 2-tetralone (1.8 mL, 14 mmol) dropwise over 45 min. After stirring at 0° C. for 2 hours, the mixture was poured slowly into crushed ice (˜50 mL). After stirring for 1 hour, the mixture was extracted with EtOAc (2×50 mL). The combined EtOAc extracts were washed with H2O (2×20 mL) and saturated brine (20 mL), dried (Na2SO4), and concentrated in vacuo to give 0.67 g (20%) of 7-oxo-5,6,7,8-tetrahydro-naphthalene-2-sulfonyl chloride as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.91 (d, 1H, J=8.1 Hz), 7.82 (s, 1H), 7.50 (d, 1H, J=8.1 Hz), 3.70 (s, 2H), 3.20 (t, 2H, J=6.6 Hz), 2.61 (t, 2H, J=6.6 Hz). The crude product was sufficiently pure and it was used in the next step without further purification.

Workup

  1. additionthe mixture was poured slowly
  2. stirringAfter stirring for 1 hour
  3. extractionthe mixture was extracted with EtOAc (2×50 mL)
  4. washThe combined EtOAc extracts were washed with H2O (2×20 mL) and saturated brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75b593a4ab7841c88bdbd5b0bd634d3d
Source dataset
uspto-grants-2009_06
Patent number
US07550467B2

Reaction notes

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