Phenylacetaldehyde → 2-Benzyl-1,3-oxathiane

HRID 963569Notes

Reaction equation

HRID 963569 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-4ca2a5b467d749cc8a168a67bb42e2c3
Source dataset
uspto-grants-1998_06
Patent number
US05763465

Reaction notes

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