o-Toluenesulfonyl chloride, 5-nitro- → 5-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenol

HRID 442947

Reaction equation

HRID 442947 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]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[S:21](Cl)(=[O:23])=[O:22]>C([O-])(O)=O.[Na+].C(OCC)C.O>[CH3:8][C:7]1[CH:9]=[C:2]([O:10][S:21]([C:13]2[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=2[CH3:11])(=[O:22])=[O:23])[CH:3]=[C:4]([OH:5])[CH:6]=1

Participants

6

Reactant 2

HCID 8457o-Toluenesulfonyl chloride, 5-nitro-HCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 544160485-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenolYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Orcinol monohydrate (2.84 g, 20.0 mmol) and 2-methyl-5-nitrobenzenesulfonyl chloride (4.71 g, 20.0 mmol) were mixed in saturated aqueous NaHCO3 (60 mL) and diethyl ether (60 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (100 mL) and extracted into ethyl acetate (3×60 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 5% ethyl acetate in dichloromethane) to give the title compound as a pale yellow solid (4.20 g, 72%). 1H-NMR (300 MHz, CDCl3) δ 8.71 (s, 1H), 8.37 (d, J=8.4 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 6.56 (s, 1H), 6.44 (s, 1H), 6.33 (s, 1H), 5.42 (s, 1H), 2.91 (s, 3H), 2.23 (s, 3H).

Workup

  1. extractionextracted into ethyl acetate (3×60 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 5% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-aee23faa0033478fbc7fd956f6c5f270
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Linked notes

Loading…