p-Toluenesulfonic acid → Ethyl ({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate

HRID 603914Notes

Reaction equation

HRID 603914 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:19])[CH2:11][S:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:20][C:21]([CH3:26])([CH2:24]O)[CH2:22][OH:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:11][S:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:23][CH2:22][C:21]([CH3:26])([CH3:24])[CH2:20][O:19]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31344Neopentyl glycolHCID 43218502Ethyl {[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]thio}acetate

Product 1

HCID 59197900Ethyl ({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ethyl {[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]thio}acetate (Method 11) (15.8 g, 0.056 mol) was dissolved in benzene (500 mL) and 2,2-dimethyl-1,3-propanediol (46.6 g, 0.45 mol) and p-toluene sulfonic acid (cat., 500 mg) were added. The mixture was stirred at reflux in a Dean-Stark apparatus for two hours, given room temperature and concentrated under reduced pressure. The resulting white solid was dissolved in CH2Cl2 (500 mL) and washed twice with water (300 mL) and brine (300 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude oil was purified by flash-chromatography (heptane:EtOAc 4:1) to afford the desired product.

Workup

  1. temperatureat reflux in a Dean-Stark apparatus for two hours
  2. customgiven room temperature
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting white solid was dissolved in CH2Cl2 (500 mL)
  5. washwashed twice with water (300 mL) and brine (300 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude oil was purified by flash-chromatography (heptane:EtOAc 4:1)

Sources & evidence

ORD record
ord-362fb4240c71418a80d80f86e22d65ba
Source dataset
uspto-grants-2011_03
Patent number
US07906502B2

Reaction notes

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