Phenacyl bromide → 1,4-Dithiin, 2,3-dihydro-5-phenyl-

HRID 839388Notes

Reaction equation

HRID 839388 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[CH2:11]([SH:14])[CH2:12][SH:13]>C1C=CC=CC=1>[C:4]1([C:2]2[S:13][CH2:12][CH2:11][S:14][CH:1]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 109021,2-Ethanedithiol

Product 1

HCID 6065711,4-Dithiin, 2,3-dihydro-5-phenyl-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

By following substantially the procedure of Example 4, Step A, phenacyl bromide (95.0 g.) and ethane-1,2-dithiol (40.0 ml.) in benzene (500 ml.) is allowed to stand for 2 days at room temperature (until gas chromatography indicates the absence of starting material). Solid by-product is removed by filtration and the filtrate is washed with aqueous sodium bicarbonate solution and water. The product solution is dried over anhydrous sodium sulfate. Solvent is removed by distillation and the residual oil is distilled at reduced pressure to afford 2-phenyl-5,6-dihydro-1,4-dithiin (47.2 g.; b.p. 140°-150° C./0.25 mm.). The product solidifies on standing and is recrystallized from methanol (m.p. 58.0°-59.0° C.).

Workup

  1. customSolid by-product is removed by filtration
  2. washthe filtrate is washed with aqueous sodium bicarbonate solution and water
  3. dry with materialThe product solution is dried over anhydrous sodium sulfate
  4. customSolvent is removed by distillation
  5. distillationthe residual oil is distilled at reduced pressure

Sources & evidence

ORD record
ord-1c3baa47e6344938baa17c58475b81cb
Source dataset
uspto-grants-1978_06
Patent number
US04094988

Reaction notes

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