p-Toluenesulfonic acid → HCID 10398395, compound

HRID 1735827Notes

Reaction equation

HRID 1735827 reaction equation
O1[C:7]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)([CH2:8][CH:9]([O:12]C)OC)[CH:2]1[C:3]([O:5][CH3:6])=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C1C=CC=CC=1>[CH3:20][C:17]1[CH:16]=[CH:15][C:14]([C:7]2[CH:8]=[CH:9][O:12][C:2]=2[C:3]([O:5][CH3:6])=[O:4])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 10085050HCID 10085050, compound

Product 1

HCID 10398395HCID 10398395, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 10.8 g of methyl 2,3-epoxy-3-(4-methylphenyl)-5,5-dimethoxypentanoate and 1.1 g of p-toluenesulfonic acid in 60 ml of anhydrous benzene is refluxed over molecular sieves for 3 h. 60 ml of ethyl acetate are added, the mixture is washed 2 times with 50 ml of a NaHCO3 saturated aqueous solution, dried over Na2SO4 and the solvent is evaporated under reduced pressure. The residue is purified by F.C. to obtain 4.2 g of a yellow oil (50% yield). 1H NMR (CDCl3), δ: 2.39 (s, 3 H), 3.85 (s, 3 H), 6.62 (d, 1 H), 7.24 (d, 2 H), 7.48 (d, 2 H), 7.56 (d, 1 H).

Workup

  1. washthe mixture is washed 2 times with 50 ml of a NaHCO3 saturated aqueous solution
  2. dry with materialdried over Na2SO4
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is purified by F.C

Sources & evidence

ORD record
ord-f5341716119c4fbda643e32458c76f68
Source dataset
uspto-grants-1996_07
Patent number
US05538987

Reaction notes

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