Hydrochloric Acid → 2-(2-Benzyloxy-5-nitrophenyl)-2-methylpropionic acid

HRID 1861968Notes

Reaction equation

C[O:2][C:3](=[O:24])[C:4]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:6])[CH3:5].[OH-].[Li+].Cl.C(OCC)(=O)C>O1CCOCC1>[CH2:17]([O:16][C:8]1[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]=1[C:4]([CH3:6])([CH3:5])[C:3]([OH:24])=[O:2])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To the compound (1.54 g) obtained in Example 562 in 1, 4-dioxane (20 ml) was added an aqueous lithium hydroxide solution (1.0M, 47 ml). The reaction mixture was heated under reflux at 100° C. for 12 h and then 2 N HCl and ethyl acetate were added. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was recrystallized from ethyl acetate to give 1.355 g of the titled compound (yield, 92%).

Workup

temperatureThe reaction mixture was heated
washThe organic layer was washed with a saturated aqueous sodium chloride solution
dry with materialdried with anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-b9a3596ee8c545d08528e60a7d260177
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06534546B1

Reaction notes

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