Hydroquinone → 2-(4-Hydroxyphenoxy)-1-(1,2-oxazolidin-2-yl)propan-1-one

HRID 543576Notes

Reaction equation

Cl[CH:2]([CH3:10])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][O:6]1)=[O:4].[C:11]1([CH:18]=[CH:17][C:15]([OH:16])=[CH:14][CH:13]=1)[OH:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:12][C:11]1[CH:18]=[CH:17][C:15]([O:16][CH:2]([CH3:10])[C:3]([N:5]2[CH2:9][CH2:8][CH2:7][O:6]2)=[O:4])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-[(±)-2-chloropropionyl]isoxazolidine (16.4 g) which was prepared as in Example 1, hydroquinone (13.2 g), anhydrous potassium carbonate (29.0 g) and dimethylformamide (100 ml) was stirred at 120° C. for 2 hours. After cooling, the reaction mixture was filtered through a suction filter to remove solid matters and the filtrate was concentrated in vacuo. The residue was washed with the addition of chloroform and 1 N hydrochloric acid and then with water and dried over anhydrous sodium sulfate. Removal of the solvent by a distillation in vacuo gave N-[(±)-2-(4-hydroxyphenoxy)propionyl]isoxazolidine (21.6 g) as a pale yellow oil which was purified by silica gel column chromatography to yield a colorless oil. nD20 =1.5412.

Workup

temperatureAfter cooling
filtrationthe reaction mixture was filtered through a suction
filtrationfilter
customto remove solid matters
concentrationthe filtrate was concentrated in vacuo
washThe residue was washed with the addition of chloroform and 1 N hydrochloric acid
dry with materialwith water and dried over anhydrous sodium sulfate
customRemoval of the solvent
distillationby a distillation in vacuo

Sources & evidence

ORD record: ord-b5e42e6d0d204c068b0b107f9d25fd97
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04447259

Reaction notes

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