Water → HCID 17871262, compound

HRID 988086Notes

Reaction equation

HRID 988086 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11](Cl)(=[O:13])=[O:12])(=[O:4])=[O:3].O.[C:16]1([OH:24])[CH:23]=[C:21]([CH3:22])[CH:20]=[C:18]([OH:19])[CH:17]=1.C([O-])(O)=O.[Na+].O>ClCCl>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([O:19][C:18]1[CH:20]=[C:21]([CH3:22])[CH:23]=[C:16]([OH:24])[CH:17]=1)(=[O:13])=[O:12])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27351782-Methanesulfonylbenzene-1-sulfonyl chlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 17871262HCID 17871262, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-methylsulfonylbenzenesulphonyl chloride (3.63 g, 14.2 mmol) and orcinol monohydrate (2.02 g, 14.2 mmol) in dichloromethane (50 mL) was added saturated NaHCO3 aqueous solution (30 mL) dropwise in 30 min. After stirred vigorously at room temperature for 3 days, water was added. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic phases were dried over Na2SO4, filtered, and concentrated to half of the volume (˜60 mL). Hexanes (30-40 mL) were added to initiate crystallization. After standing overnight, the mixture was filtered, and the solid was rinsed with small amount of diethyl ether and dichloromethane to give the title compound as a pale pink solid (2.18 g, 44.8%). 1H NMR (CDCl3) δ 8.43 (dd, 1H, J=1.3, 7.9 Hz), 8.11 (dd, 1H, J=1.3, 7.9 Hz), 7.87 (td, 1H, J=1.4, 7.7 Hz), 7.73 (td, 1H, J=1.4, 7.7 Hz), 6.58 (s, 1H), 6.55 (s, 1H), 6.51 (s, 1H), 3.45 (s, 3H), 2.21 (s, 3H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to half of the volume (˜60 mL)
  6. additionHexanes (30-40 mL) were added
  7. customcrystallization
  8. waitAfter standing overnight
  9. filtrationthe mixture was filtered
  10. washthe solid was rinsed with small amount of diethyl ether and dichloromethane

Sources & evidence

ORD record
ord-8f23f75183074a24b257619d80a0b138
Source dataset
uspto-grants-2003_10
Patent number
US06635637B2

Reaction notes

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