Benzenesulfonyl chloride, 2,5-dimethyl- → HCID 53837258, compound

HRID 442936Notes

Reaction equation

HRID 442936 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:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[S:19](Cl)(=[O:21])=[O:20]>C([O-])(O)=O.[Na+].C(OCC)C.O>[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[S:19]([O:5][C:4]1[CH:3]=[C:2]([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=1)(=[O:20])=[O:21]

Participants

6

Reactant 2

HCID 87910Benzenesulfonyl chloride, 2,5-dimethyl-HCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 53837258HCID 53837258, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Orcinol monohydrate (1.42 g, 10.0 mmol) and 2,5-dimethylbenzenesulfonyl chloride (2.05 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 (2.10 g, 72%). 1H-NMR (300 MHz, CDCl3) δ 7.65 (s, 1H), 7.29 (m, 1H), 7.25 (m, 1H), 6.50 (s, 1H), 6.38 (s, 1H), 6.30 (s, 1H), 5.27 (br s, 1H), 2.30 (s, 3H), 2.18 (s, 3H), 2.03 (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-7dfbc2158a6e451b809d0d7f577b1b03
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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