Benzene → HCID 12507637, compound

HRID 426845Notes

Reaction equation

HRID 426845 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][O:6][C:5]1=[O:9])(=[O:3])[CH3:2].[CH:10]1[CH:11]=[CH:12][C:13]2[NH:18][CH:17]=[C:16]([CH2:19][CH2:20]O)[C:14]=2[CH:15]=1.C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:2][C:1]1([CH:4]2[CH2:8][CH2:7][O:6][C:5]2=[O:9])[C:17]2[NH:18][C:13]3[C:14]([C:16]=2[CH2:19][CH2:20][O:3]1)=[CH:15][CH:10]=[CH:11][CH:12]=3

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acid2×HCID 106012-AcetylbutyrolactoneHCID 10685Tryptophol

Product 1

HCID 12507637HCID 12507637, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution consisting of 3-acetyldihydro-2(3H)-furanone (25.6 g, 0.2 mole), tryptophol (32.2 g, 0.2 mole) and benzene (700 ml), p-toluenesulfonic acid (0.50 g) is added. The flask is equipped with a water separator and a condenser. The mixture is stirred at reflux for one hr. More p-toluenesulfonic acid (0.50 g) is added and the solution is refluxed for 18 hr. The dark solution is cooled and stirred in presence of silica gel (100 g) for 5 min. The mixture is filtered on diatomaceous earth and charcoal. The silica gel is washed with diethyl ether (2×100 ml) and the filtrates are evaporated to afford an oil which is a mixture of two diasteroisomers of the title compound. If desired, the latter oil can be crystallizated from methanol to obtain crystals (17 g) of isomer A of the title compound, mp 162°-164° C. The mother liquor of this crystallization is evaporated to obtain a residue (20 g) containing mainly isomer B of the title compound.

Workup

  1. additionis added
  2. temperatureat reflux for one hr
  3. temperaturethe solution is refluxed for 18 hr
  4. temperatureThe dark solution is cooled
  5. stirringstirred in presence of silica gel (100 g) for 5 min
  6. filtrationThe mixture is filtered on diatomaceous earth and charcoal
  7. washThe silica gel is washed with diethyl ether (2×100 ml)
  8. customthe filtrates are evaporated
  9. customto afford an oil which

Sources & evidence

ORD record
ord-b8eda8d1c6434fe6aa085180eafe7d03
Source dataset
uspto-grants-1979_10
Patent number
US04171443

Reaction notes

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