2-Cyanobenzenesulfonyl Chloride → 3-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propanol Hydrochloride

HRID 1059461Notes

Reaction equation

HRID 1059461 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)(=[O:11])=[O:10])#[N:2].O.[C:22]1(O)C=C(C)C=[C:24]([OH:25])[CH:23]=1.C(C1C=CC=CC=1S([Cl:42])(=O)=O)#N>C([O-])(O)=O.[Na+].C(OCC)C.O>[ClH:42].[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[O:20][CH2:22][CH2:23][CH2:24][OH:25])(=[O:11])=[O:10])#[N:2]

Participants

7

Reactant 3

HCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 3083941Resorcinol, 5-methyl-, monohydrateHCID 227226433-(2-Cyanophenylsulfonyloxy)-5-methylphenol

Product 1

HCID 186697053-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propanol HydrochlorideYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-(2-Cyanophenylsulfonyloxy)-5-methylphenol: Orcinol monohydrate (1.42 g, 10.0 mmol) and 2-cyanobenzenesulfonyl chloride (2.02 g, 10.0 mmol) were mixed in saturated NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at room 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 5% ethyl acetate in dichloromethane) to give the title compound as a white solid (1.65 g, 57%). 1H-NMR (300 MHz, CDCl3) δ 8.07 (m, 1H), 7.94 (m, 1H), 7.75-7.80 (m, 2H), 6.57 (s, 1H), 6.53 (s, 1H), 6.49 (s, 1H), 5.69 (br s, 1H), 2.22 (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 5% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-b6531c9ea60c4c6a95928a78653eabc6
Source dataset
uspto-grants-2003_02
Patent number
US06518310B2

Reaction notes

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