p-Toluenesulfonic acid → HCID 54011131, compound

HRID 2050411Notes

Reaction equation

HRID 2050411 reaction equation
[C:1]([CH:9]([CH2:13]OC)[CH2:10][O:11][CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CCOCC.O>[C:1]([C:9]([CH2:10][O:11][CH3:12])=[CH2:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acid3×HCID 10340Sodium CarbonateHCID 54400839HCID 54400839, compound

Product 1

HCID 54011131HCID 54011131, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

An 84 g sample of 91% pure 2-benzoyl-1,3-dimethoxy propane 1 was heated with 4.2 g (5 wt %) of p-toluene sulfonic acid (p-TSA) to 80° with stirring. After 5 hr. a second 4.2 g sample of p-TSA was added. A third p-TSA addition of 2 g was made after another 5 hr. This mixture was left stirring for 6.5 hrs longer and then cooled. The reaction mixture was diluted with ml of Et2O and 100 ml H2O added. This mixture was then neutralized to pH=6-7 with dilute Na2CO3 and the organic layer dried over MgSO4. Filtration and removal of the ether in vacuo left an orange liquid, 2, which was distilled at 0.1 mm and 76° C. Yield: 73%. Purity: 93%.

Workup

  1. waitwas made after another 5 hr
  2. waitThis mixture was left
  3. stirringstirring for 6.5 hrs longer
  4. temperaturecooled
  5. additionadded
  6. dry with materialthe organic layer dried over MgSO4
  7. filtrationFiltration and removal of the ether in vacuo
  8. waitleft an orange liquid, 2, which
  9. distillationwas distilled at 0.1 mm and 76° C

Sources & evidence

ORD record
ord-e7849eb732c944b1b4453d8a21065531
Source dataset
uspto-grants-1991_05
Patent number
US05013483

Reaction notes

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