Sodium Hydroxide → 4-[4-(1-Methoxycyclopropyl)-phenylethynyl]-benzoic Acid

HRID 395099Notes

Reaction equation

HRID 395099 reaction equation
[CH3:1][O:2][C:3]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4]1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:1][O:2][C:3]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:23][CH:24]=3)=[CH:10][CH:11]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22568838Ethyl 4-[4-(1-methoxycyclopropyl)-phenylethynyl]-benzoate2×

Product 1

HCID 98791434-[4-(1-Methoxycyclopropyl)-phenylethynyl]-benzoic AcidYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl 4-[4-(1-methoxycyclopropyl)-phenylethynyl]-benzoate (Compound 67, 110.0 mg, 0.34 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (160.0 mg, 4.0 mmols, 2.0 mL of a 2N aqueous solution) and stirred overnight at room temperature. Work-up afforded 85.0 mg (86%) of the title compound as an orange solid.

Sources & evidence

ORD record
ord-89381a39250744abad8009cc185ddd19
Source dataset
uspto-grants-2003_08
Patent number
US06603019B2

Reaction notes

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