Thionyl Chloride → HCID 63432053, compound

HRID 1877217Notes

Reaction equation

HRID 1877217 reaction equation
[CH:1]1([CH:7]([C:9]2[CH:13]=[C:12]([CH3:14])[S:11][C:10]=2[CH3:15])O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:18])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:18][CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:9]1[CH:13]=[C:12]([CH3:14])[S:11][C:10]=1[CH3:15]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 61088924HCID 61088924, compound

Product 1

HCID 63432053HCID 63432053, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of cyclohexyl(2,5-dimethylthiophen-3-yl)methanol (643 mg) synthesized above in toluene (10 mL) was added thionyl chloride (314 μL), and the mixture was stirred at room temperature for 6 hr. The reaction mixture was poured into ice-cooled saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (653 mg, 94%) as a brown oil.

Workup

  1. additionThe reaction mixture was poured into ice-
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-31dcc03a9fc5421aad75ad45431b2f0a
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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