3-Chlorobenzenesulphonyl chloride → 3-(3-Chlorophenylsulfonyloxy)-5-methylphenol

HRID 442944Notes

Reaction equation

HRID 442944 reaction equation
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[Cl: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>[Cl:11][C:12]1[CH:13]=[C:14]([S:18]([O:5][C:4]2[CH:3]=[C:2]([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=2)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 540176793-(3-Chlorophenylsulfonyloxy)-5-methylphenolYield 69.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Orcinol monohydrate (1.42 g, 10.0 mmol) and 3-chlorobenzenesulfonyl chloride (2.21 g, 10.0 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 (3×50 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 2% ethyl acetate in dichloromethane) to give the title compound as a pale yellow oil (2.08 g, 69%). 1H-NMR (300 MHz, CDCl3) δ 7.86 (s, 1H), 7.74 (d, J=7.8 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.48 (t, J=8.0 Hz, 1H), 6.57 (s, 1H), 6.40 (s, 1H), 6.33 (s, 1H), 5.32 (s, 1H), 2.24 (s, 3H).

Workup

  1. extractionextracted into ethyl acetate (3×50 mL)
  2. washThe organic phase was washed with brine (2×50 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 2% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-fcbda711bffa48c3bb9d266f630745d4
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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