Hydrochloric Acid → 4,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazoline

HRID 1082009Notes

Reaction equation

[CH3:1][C:2]1([CH3:24])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][O:20]COC)=[CH:15][CH:14]=2)=[N:3]1.Cl.C(=O)([O-])O.[Na+]>CO>[CH3:1][C:2]1([CH3:24])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[CH:15][C:16]([CH2:19][OH:20])=[CH:17][CH:18]=2)=[N:3]1

Participants

Conditions

Temperature: 40 °C

Procedure

2.62 g (8.05 mmol) of 4,4-dimethyl-2-(4'-methoxymethoxymethylbiphenyl-2-yl)oxazoline was dissolved in methanol (20 ml). 6N hydrochloric acid (10 ml) was added thereto, followed by stirring at 40° C. for 2 hours. The reaction liquid was poured into a saturated aqueous solution of sodium hydrogencarbonate, followed by the extraction with chloroform. After washing with water and drying, vacuum concentration was conducted. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 2.20 g of the title compound as a crystal (yield 97%).

Workup

customThe reaction liquid
extractionfollowed by the extraction with chloroform
washAfter washing with water
customdrying
concentrationvacuum concentration
customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Sources & evidence

ORD record: ord-fd3ce3a143ce4ab5baafc67e27dea441
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05587504

Reaction notes

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