Thiophenol → HCID 15339021, compound

HRID 1785765Notes

Reaction equation

HRID 1785765 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:17])C=1.[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl.C(OCC)C>[CH:3]1([CH:1]([OH:17])[CH2:2][S:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 12757VinylcyclohexaneHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 15339021HCID 15339021, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A room temperature solution of vinylcyclohexane (1.71 g, 15.5 mmol) in dichloromethane (20 mL) was treated with 70% mCPBA (4.90 g, 19.9 mmol), stirred for 3 hours, diluted with diethyl ether (100 mL), washed with saturated NaHCO3 and brine, dried (MgSO4), filtered, and concentrated. The concentrate was dissolved in 1,2-dichloroethane (20 mL), treated with thiophenol (1.8 g, 16.3 mmol), heated to 80° C., stirred for 5 hours, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20% ethyl acetate/hexanes to provide the desired product. MS (DCI/NH3) m/e 254 (M+NH4).

Workup

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe concentrate was dissolved in 1,2-dichloroethane (20 mL)
  6. stirringstirred for 5 hours
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8ad66315b8f04b8281338d7e782a4e53
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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