Hydrochloric Acid → 3,5-Bis[(2-methylphenyl)methylidene]thian-4-one

HRID 1704728Notes

Reaction equation

HRID 1704728 reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[C:8]1([CH3:16])[C:9]([CH:14]=O)=[CH:10][CH:11]=[CH:12][CH:13]=1.Cl>C(O)C>[CH3:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH:16]=[C:3]1[C:4](=[O:7])[C:5](=[CH:16][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[CH2:6][S:1][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 107222-MethylbenzaldehydeHCID 66173Tetrahydrothiopyran-4-one

Product 1

HCID 543246713,5-Bis[(2-methylphenyl)methylidene]thian-4-oneYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tetrahydro-4H-thiopyran-4-one (9.3 g, 0.08 mole) and o-tolualdehyde (25 g, 0.20 mole) are dissolved in 60 ml of ethanol and treated with concentrated hydrochloric acid (6 ml). After heating at reflux temperature for 4 hours, the mixture is cooled and product is collected by filtration. The combined filtrate and washings (ethanol) are concentrated to the original volume and additional concentrated hydrochloric acid (4 ml) is added and the mixture is refluxed for 4 hours. This procedure is repeated 3 times. The combined crude material (23 g) is recrystallized from chloroform/ethanol/H2O to give 22.5 g (88%) of product, m.p. 123°-125°.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux temperature for 4 hours
  3. temperaturethe mixture is cooled
  4. filtrationproduct is collected by filtration
  5. concentrationThe combined filtrate and washings (ethanol) are concentrated to the original volume and additional concentrated hydrochloric acid (4 ml)
  6. additionis added
  7. temperaturethe mixture is refluxed for 4 hours
  8. customis recrystallized from chloroform/ethanol/H2O

Sources & evidence

ORD record
ord-3f841df869c04f80a9243eeb8dd830bc
Source dataset
uspto-grants-1978_11
Patent number
US04127667

Reaction notes

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