Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 6-(beta-Chloroethoxy)-1-tetralone

HRID 1859766Notes

Reaction equation

HRID 1859766 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:19][CH2:20][CH2:21]OS(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+]>CN(C=O)C.C(Cl)Cl.CCOCC.O>[Cl:19][CH2:20][CH2:21][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2

Participants

9

Reactant 4

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 120429826-(beta-Chloroethoxy)-1-tetraloneYield 96%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-hydroxy tetralone (2.0 g, 12.3 mmol) in DMF (50 mL) was added dry cesium carbonate (8.02 g, 24.6 mmol). Neat 2-chloroethyl-p-toluensulfonate (3.49 g, 14.9 mmol) was added to this mixture and the reaction stirred at room temperature for 58 hours. The reaction was poured into 200 mL of water and to this mixture was added 10 mL of 1N NaOH followed by 200 mL of Et2O. The mixture stirred at room temperature for 2 hours. The aqueous portion was separated and extracted with Et2O (3×200 mL). The combined organic portions were washed successively with 1N NaOH (2×100 mL), water (2×100 mL), and brine, dried, filtered, and concentrated under vacuum to give 5.07 g of a faintly orange solid. The solid was dissolved in minimal DCM and chromatographed (silica gel, 190 g, DCM). The appropriate fractions were pooled and concentrated under vacuum to afford 2.65 g (96%) of a white crystalline solid:

Workup

  1. stirringThe mixture stirred at room temperature for 2 hours
  2. customThe aqueous portion was separated
  3. extractionextracted with Et2O (3×200 mL)
  4. washThe combined organic portions were washed successively with 1N NaOH (2×100 mL), water (2×100 mL), and brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto give 5.07 g of a faintly orange solid
  9. customchromatographed (silica gel, 190 g, DCM)
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e49b6589fa3e414bbf74a21647cc2097
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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