3-Methylbenzenesulphonyl chloride → HCID 10934765, compound

HRID 442924Notes

Reaction equation

HRID 442924 reaction equation
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[CH3:11][C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1>C([O-])(O)=O.[Na+].C(OCC)C.O>[CH3:8][C:7]1[CH:9]=[C:2]([O:10][S:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([CH3:11])[CH:13]=2)(=[O:20])=[O:19])[CH:3]=[C:4]([OH:5])[CH:6]=1

Participants

6

Reactant 2

HCID 27345953-Methylbenzenesulphonyl chlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 10934765HCID 10934765, compoundYield 94.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Orcinol monohydrate (1.42 g, 10.0 mmol) and 3-methylbenzenesulfonyl chloride (1.60 g, 8.0 mmol) were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3×40 mL). The organic phase was washed with brine (2×30 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane) to give the title compound as a yellow oil (2.1 g, 76%). 1H-NMR (300 MHz, CDCl3) δ 7.68 (s, 1H), 7.64 (d, J=7.9 Hz, 1H), 7.45 (t, J=7.8 Hz, 1H), 7.40 (t, J=7.6 Hz, 1H), 6.54 (s, 1H), 6.39 (s, 1H), 6.32 (s, 1H), 5.33 (s, 1H), 2.41 (s, 3H), 2.21 (s, 3H).

Workup

  1. extractionextracted into ethyl acetate (3×40 mL)
  2. washThe organic phase was washed with brine (2×30 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvent in vacuo
  5. customthe residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-71004d10adc34bdd82d652e390f27bb6
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

Loading…