Hydrochloric Acid → HCID 13579045, compound

HRID 980079Notes

Reaction equation

HRID 980079 reaction equation
[CH3:1][C:2]1([CH3:10])[S:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[CH2:3]1.[C:11](Cl)(=[O:15])[CH2:12][CH2:13][CH3:14].Cl>N1C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[CH3:1][C:2]1([CH3:10])[S:7][C:6](=[O:8])[CH:5]([C:11](=[O:15])[CH2:12][CH2:13][CH3:14])[C:4](=[O:9])[CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8855Butyryl chlorideHCID 2820422HCID 2820422, compound

Product 1

HCID 13579045HCID 13579045, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1049PyridineSolvent

Procedure

9.6 g (0.07 mol) of zinc chloride are first added to 5 g (0.035 mol) of 6,6-dimethyltetrahydrothiopyran-2,4-dione in 100 ml of pyridine, after which 3.7 g (0.03 mol) of butyryl chloride are added dropwise. When the addition is complete, the mixture is heated to the reflux temperature for 4 hours, and the cooled reaction mixture is poured into 200 ml of semi-concentrated hydrochloric acid, the mixture is extracted several times with dichloromethane, the combined organic phases are dried over magnesium sulphate, and the solvent is removed in vacuo. 2.9 g (36.6% of theory) of 6,6-dimethyl-3-butyryltetrahydrothiopyran-2,4-dione are obtained as an oil.

Workup

  1. additionWhen the addition
  2. temperaturethe mixture is heated to the reflux temperature for 4 hours
  3. customthe cooled reaction mixture
  4. extractionthe mixture is extracted several times with dichloromethane
  5. dry with materialthe combined organic phases are dried over magnesium sulphate
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7062a69809644b6ea2f23945ebe467d3
Source dataset
uspto-grants-1987_01
Patent number
US04636245

Reaction notes

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