Hydrochloric Acid → 5-[3-(4-Hydroxy-3-methoxyphenyl)propyl]-2,4-oxazolidinedione

HRID 1584335Notes

Reaction equation

C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH:14]2[O:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])=[CH:7][C:6]=1[O:21][CH3:22])(C)C.Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH:14]2[O:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])=[CH:7][C:6]=1[O:21][CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of titanium tetrachloride (TiCl4) (10.6 g) in dichloromethane (10 ml) was added dropwise, at 0° C., to a solution of 5-[3-(4-isopropoxy-3-methoxy-phenyl)propyl]-2,4-oxazolidinedione (4.3 g) in dichloromethane (130 ml). The mixture was stirred for one hour at 0° C., which was poured into 2N HCl, followed by stirring for 15 minutes at room temperature. The organic layer was separated, and the aqueous layer was subjected to extraction with chloroform. The organic layers were combined, washed successively with water, 2N HCl and water, which was dried (MgSO4), followed by concentration to yield 5-[3-(4-hydroxy-3-methoxyphenyl)propyl]-2,4-oxazolidinedione (2.8 g, 76%). Recrystallization of the product from ethanol-hexane gave colorless prisms, m.p.147-148° C.

Workup

stirringby stirring for 15 minutes at room temperature
customThe organic layer was separated
extractionthe aqueous layer was subjected to extraction with chloroform
washwashed successively with water, 2N HCl and water, which
dry with materialwas dried (MgSO4)
concentrationfollowed by concentration

Sources & evidence

ORD record: ord-716fb1edf1f743da838b0944759ef5cf
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932601

Reaction notes

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