p-Toluenesulfonic acid → HCID 86648276, compound

HRID 1915996Notes

Reaction equation

HRID 1915996 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:19]=[CH:18][C:7](/[CH:8]=[CH:9]/[C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[CH:6][C:5]=1[O:20][CH3:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[CH:3]([C:4]1[CH:19]=[CH:18][C:7](/[CH:8]=[CH:9]/[C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[CH:6][C:5]=1[O:20][CH3:21])=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67480194HCID 67480194, compound

Product 1

HCID 86648276HCID 86648276, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-4-(4-(dimethoxymethyl)-3-methoxystyryl)benzonitrile (70 mg, 0.227 mmol) in aqueous THF (5 ml water/25 ml THF) was added p-toluenesulfonic acid (1 mg, 0.02 eq.) and the mixture was refluxed for 30 minutes. The mixture was concentrated under reduced pressure, extracted with EtOAc (3×), dried, and the solvent was removed in vacuum to give the desired product 99% pure by GC-MS. MS (EI+): 263 (100%, M+); 246 (40%), 232, 216, 203 (60%), 190 (65%), 176, 140, 88.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. concentrationThe mixture was concentrated under reduced pressure
  3. extractionextracted with EtOAc (3×)
  4. customdried
  5. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-ced254d8c14642caa564a57a62f1c744
Source dataset
uspto-grants-2013_12
Patent number
US08617515B2

Reaction notes

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