Toluene → 2-(4-Methylsulfanyl-phenyl)-[1,3]dioxane

HRID 1828705Notes

Reaction equation

HRID 1828705 reaction equation
C[C:2]1[CH:9]=[CH:8][C:5](C=S)=CC=1.[CH:10]([OH:14])([OH:13])[CH2:11][CH3:12].C1(C)[C:16]([S:21](O)(=O)=O)=CC=CC=1.[C:26]1([CH3:32])C=CC=C[CH:27]=1>>[CH3:16][S:21][C:9]1[CH:8]=[CH:5][C:11]([CH:10]2[O:14][CH2:32][CH2:26][CH2:27][O:13]2)=[CH:12][CH:2]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 69252-Methylbenzenesulfonic acidHCID 134919PropanediolHCID 181775354-Methylthiobenzaldehyde

Product 1

HCID 220577452-(4-Methylsulfanyl-phenyl)-[1,3]dioxane

Procedure

In a round bottom flask equipped with Dean-Stark apparatus, a mixture of 4-methylthio benzaldehyde (5 g, 32.8 mmol), propanediol (2.75 g, 36.1 mmol), and toluenesulfonic acid (550 mg, 3.28 mmol) in toluene (300 mL, anhydrous) is heated at reflux under N2. After 5 h, the reaction mixture is cooled to room temperature, and washed with saturated aqueous NaHCO3 (3×40 mL). The organic phase is concentrated and the obtained crude product is purified by silica gel column chromatography (15% EtOAc in hexanes) to give 2-(4-methylsulfanyl-phenyl)-[1,3]dioxane as a yellow oil.

Workup

  1. customIn a round bottom flask equipped with Dean-Stark apparatus
  2. temperatureis heated
  3. temperatureat reflux under N2
  4. washwashed with saturated aqueous NaHCO3 (3×40 mL)
  5. concentrationThe organic phase is concentrated
  6. customthe obtained crude product
  7. customis purified by silica gel column chromatography (15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-dec830c2dd68469d9c4c4bb03f83d941
Source dataset
uspto-grants-2006_06
Patent number
US07060697B2

Reaction notes

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