Benzyl Alcohol → 4-Benzyloxy-3-pyrrolin-2-one

HRID 231887

Reaction equation

[CH3:1][O:2][C:3]1[CH2:7][NH:6][C:5](=[O:8])[CH:4]=1.C(O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CS(O)(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:2][C:3]1[CH2:7][NH:6][C:5](=[O:8])[CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5.7 g of 4-methoxy-3-pyrrolin-2-one and 10.8 g of benzyl alcohol were mixed with 0.4 g of methane sulfonic acid and stirred for 24 hours at 80° C. and 20 mbars. Then the reaction solution was mixed with 50 ml of ice water and 100 ml of methylene chloride and neutralized with 4 ml of saturated NaHCO3 solution. The aqueous phase was extracted twice more with 50 ml each of methylene chloride. After drying of the organic phase over Na2SO4 and distilling off of the solvent, the residue was mixed with 150 ml of ice water, heated to 100° C. and 100 ml of water-benzyl alcohol was azeotropically distilled off. The crystals precipitated during the cooling were recrystallized hot from 50 ml of toluene. 6.7 g of white, crystalline product with a melting point of 147° to 148° was obtained. For the product:

Workup

extractionThe aqueous phase was extracted twice more with 50 ml each of methylene chloride
dry with materialAfter drying of the organic phase over Na2SO4
distillationdistilling off of the solvent
additionthe residue was mixed with 150 ml of ice water
temperatureheated to 100° C.
distillation100 ml of water-benzyl alcohol was azeotropically distilled off
customThe crystals precipitated during the cooling
customwere recrystallized hot from 50 ml of toluene
custom6.7 g of white, crystalline product with a melting point of 147° to 148° was obtained

Sources & evidence

ORD record: ord-8caa1fe527544a2e9c53fbfaa7fadd98
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04849528

Linked notes

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