Phenylacetaldehyde → 2-Benzyl-1,3-oxathiane

HRID 265300Notes

Reaction equation

HRID 265300 reaction equation
C1(C)C=C[C:4]([S:7](O)(=O)=O)=[CH:3][CH:2]=1.[C:12]1([CH2:18][CH:19]=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[C:12]1([CH2:18][CH:19]2[S:7][CH2:4][CH2:3][CH2:2][O:20]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 998PhenylacetaldehydeHCID 6101p-Toluenesulfonic acid

Product 1

HCID 123959182-Benzyl-1,3-oxathiane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the thiol (14.67 g) from step a) in toluene (200 ml) was added p-toluenesulphonic acid (1 g) and phenylacetaldehyde (18.3 ml). The reaction was refluxed using a Dean and Stark apparatus. After the appropriate amount of water had been collected the reaction mixture was cooled, washed with saturated sodium bicarbonate, saturated brine and dried (K2CO3). The crude product was distilled (bp 100°-110°/0.3 mbars) to give a yellow liquid (19.65 g).

Workup

  1. temperatureThe reaction was refluxed
  2. customAfter the appropriate amount of water had been collected the reaction mixture
  3. temperaturewas cooled
  4. washwashed with saturated sodium bicarbonate, saturated brine
  5. dry with materialdried (K2CO3)
  6. distillationThe crude product was distilled (bp 100°-110°/0.3 mbars)

Sources & evidence

ORD record
ord-5425f26ac9104f96946daa35a5859e89
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Reaction notes

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